1838-39-7

Basic information

• Product Name: Ethyl 4-(ethoxycarbonyl)piperidine-1-acetate
• Synonyms: PIPERIDINE-1,4-DICARBOXYLIC ACID DIETHYL ESTER;ethyl 4-(ethoxycarbonyl)piperidine-1-acetate;N-Ethyl aletate-4-Ethy Piperidinelarboxylate ;4-[Ethoxycarbonyl]-1-piperidineacetic acid ethyl ester;Ethyl 1-ethoxycarbonylmethyl-iso-nipecotate;Ethyl [4-(ethoxycarbonyl)piperidin-1-yl]acetate, 4-(Ethoxycarbonyl)-1-(2-ethoxy-2-oxoethyl)piperidine;1-Piperidineaceticacid, 4-(ethoxycarbonyl)-, ethyl ester;1-(2-ethoxy-2-keto-ethyl)isonipecotic acid ethyl ester
• CAS NO: 1838-39-7
• Molecular Formula: C₁₂H₂₁NO₄
• Molecular Weight: 243.3
• EINECS: 217-412-3
• Mol File: 1838-39-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 309.5 °C at 760 mmHg
• Flash Point: 141 °C
• Appearance: /
• Density: 1.077g/cm³
• Vapor Pressure: 0.000637mmHg at 25°C
• Refractive Index: 1.466
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.35±0.10(Predicted)
• CAS DataBase Reference: Ethyl 4-(ethoxycarbonyl)piperidine-1-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4-(ethoxycarbonyl)piperidine-1-acetate(1838-39-7)
• EPA Substance Registry System: Ethyl 4-(ethoxycarbonyl)piperidine-1-acetate(1838-39-7)

Safety Data

• Hazardous Substances Data: 1838-39-7(Hazardous Substances Data)

Usage

Uses

Ethyl 1-?(2-?Ethoxy-?2-?oxoethyl)?-?4-?piperidinecarboxylat?e is a reagent used in the is a reagent used in the preparation of quinuclidine derivatives.

InChI:InChI=1/C12H21NO4/c1-3-16-11(14)9-13-7-5-10(6-8-13)12(15)17-4-2/h10H,3-9H2,1-2H3

Synthetic route

chloroacetic acid ethyl ester (105-39-5) + piperidine-4-carboxylic acid ethyl ester hydrochloride → ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7)

Conditions	Yield
Stage #1: piperidine-4-carboxylic acid ethyl ester hydrochloride With potassium carbonate In acetonitrile at 20℃; for 0.166667h; Stage #2: chloroacetic acid ethyl ester In acetonitrile at 20℃; for 5.5h;	93.1%

4-carbethoxypiperidine (1126-09-6) + chloroacetic acid ethyl ester (105-39-5) → ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7)

Conditions	Yield
With potassium carbonate

isonicotinic acid ethylester (1570-45-2) → ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Raney nickel; dioxane / 175 - 180 °C / 91938.4 Torr / Hydrogenation 2: K2CO3 View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-Quinuclidinone (3731-38-2)

Conditions	Yield
With potassium; toluene anschliessend mit konz. Salzsaeure;
With potassium ethoxide; toluene anschliessend mit konz. Salzsaeure;

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 2-ethoxycarbonyl-3-quinuclidinone (34286-16-3)

Conditions	Yield
With potassium ethoxide; toluene
With potassium tert-butylate In toluene for 4.5h; Dieckmann Condensation; Reflux; Inert atmosphere;

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-(3-oxo-quinuclidin-2-yl)-propionitrile (99169-54-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium ethylate; toluene / anschliessend mit konz. Salzsaeure 2: methanol. KOH; tert-butyl alcohol View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 2,2-bis-(2-cyano-ethyl)-quinuclidin-3-ol (105788-47-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium ethylate; toluene / anschliessend mit konz. Salzsaeure 2: tert-butyl alcohol; acrylonitrile; methanol. KOH 3: LiAlH4; diethyl ether; benzene / 65 - 70 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3,3'-(3-oxo-quinuclidine-2,2-diyl)-di-propionitrile (100705-63-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium ethylate; toluene / anschliessend mit konz. Salzsaeure 2: tert-butyl alcohol; acrylonitrile; methanol. KOH View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3,3'-(3-oxo-quinuclidine-2,2-diyl)-di-propionic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium ethylate; toluene / anschliessend mit konz. Salzsaeure 2: tert-butyl alcohol; acrylonitrile; methanol. KOH 3: acetic acid; concentrated aqueous HCl View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → Quinuclidine (100-76-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: hydrazine hydrate; sodium ethylate; ethanol / 175 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → quinuclidinyl benzilate (6581-06-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: sodium; toluene / Behandeln mit Chlor-diphenyl-acetylchlorid und Erwaermen des Reaktionsgemisches mit wss. Salzsaeure View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 2,2-diphenyl-pent-4-enoic acid quinuclidin-3-yl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: sodium; toluene / Behandeln mit 2,2-Diphenyl-pent-4-enoylchlorid View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-bromo-quinuclidine; hydrobromide (99310-69-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: concentrated aqueous hydrobromic acid / 180 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → fluorene-9-carboxylic acid quinuclidin-3-yl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: benzene View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → (S)-quinuclidin-3-ol (3684-26-2, 25333-42-0, 34583-34-1, 1619-34-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: (1S)-2-oxo-bornane-10-sulfonic acid View Scheme
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h 4.1: 2 h / 20 °C 5.1: ethanol; water / 0.33 h / 50 °C 6.1: sodium hydroxide / water / 1 h / 70 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → (R)-quinuclidin-3-ol (25333-42-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: (1S)-2-oxo-bornane-10-sulfonic acid View Scheme
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h 4.1: 2 h / 20 °C 5.1: ethanol; water / 0.33 h / 50 °C 6.1: sodium hydroxide / water / 1 h / 70 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-quinuclidinol (1619-34-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether View Scheme
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → (R)-diphenylacetic acid quinuclidin-3-yl ester (62078-97-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: (1S)-2-oxo-bornane-10-sulfonic acid 4: benzene View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-(Diphenylacetyloxy)quinuclidine (62078-97-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: benzene View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-quinuclidinone hydrochloride (1193-65-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-acetoxyquinuclidine (827-61-2, 59653-40-6, 59653-42-8, 72353-53-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h 4.1: 2 h / 20 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → (R)-3-acetoxyquinuclidinium L-tartrate

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h 4.1: 2 h / 20 °C 5.1: ethanol; water / 0.33 h / 50 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → (S)-3-acetoxyquinuclidinium D-tartrate

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h 4.1: 2 h / 20 °C 5.1: ethanol; water / 0.33 h / 50 °C View Scheme

Upstream product

• 105-39-5 chloroacetic acid ethyl ester 
• 1570-45-2 isonicotinic acid ethylester 
• 1126-09-6 4-carbethoxypiperidine 

Downstream Products

• 1193-65-3 3-quinuclidinone hydrochloride 
• 827-61-2 3-acetoxyquinuclidine 
• 62078-97-1 3-(Diphenylacetyloxy)quinuclidine 
• 62078-97-1 (R)-diphenylacetic acid quinuclidin-3-yl ester 
• 1619-34-7 3-quinuclidinol 
• 25333-42-0 (R)-quinuclidin-3-ol 
• 3684-26-2 (S)-quinuclidin-3-ol 
• 6581-06-2 quinuclidinyl benzilate 
• 100-76-5 Quinuclidine 
• 34286-16-3 2-ethoxycarbonyl-3-quinuclidinone 
• 3731-38-2 3-Quinuclidinone 

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