4-benzyloxy-N-[3-(1-cyclohexylmethyl-piperidin-4-ylamino)-propyl]-3,5-dimethoxy-benzamide

Base Information

• Chemical Name: 4-benzyloxy-N-[3-(1-cyclohexylmethyl-piperidin-4-ylamino)-propyl]-3,5-dimethoxy-benzamide
• CAS No.: 328039-93-6
• Molecular Formula: C₃₁H₄₅N₃O₄
• Molecular Weight: 523.716

Synonyms:4-benzyloxy-N-[3-(1-cyclohexylmethyl-piperidin-4-ylamino)-propyl]-3,5-dimethoxy-benzamide

Chemical Property of 4-benzyloxy-N-[3-(1-cyclohexylmethyl-piperidin-4-ylamino)-propyl]-3,5-dimethoxy-benzamide

Chemical Property:

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Technology Process of 4-benzyloxy-N-[3-(1-cyclohexylmethyl-piperidin-4-ylamino)-propyl]-3,5-dimethoxy-benzamide

There total 3 articles about 4-benzyloxy-N-[3-(1-cyclohexylmethyl-piperidin-4-ylamino)-propyl]-3,5-dimethoxy-benzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 48.2%

4-(benzyloxy)-3,5-dimethoxybenzoic acid (14588-60-4) + (3-amino-propyl)-(1-cyclohexylmethyl-piperidin-4-yl)-carbamic acid tert-butyl ester (516471-66-2) → 4-benzyloxy-N-[3-(1-cyclohexylmethyl-piperidin-4-ylamino)-propyl]-3,5-dimethoxy-benzamide (328039-93-6)

Guidance literature:

4-(benzyloxy)-3,5-dimethoxybenzoic acid; (3-amino-propyl)-(1-cyclohexylmethyl-piperidin-4-yl)-carbamic acid tert-butyl ester; With polymer-bound EDC; In chloroform; at 20 ℃; for 6h;

With acidic ion exchange resin P-SO₃H; In chloroform; for 5h;

DOI:10.1016/S0968-0896(02)00207-9

Reference yield:

(3-chloro-propyl)-(1-cyclohexylmethyl-piperidin-4-yl)-amine → 4-benzyloxy-N-[3-(1-cyclohexylmethyl-piperidin-4-ylamino)-propyl]-3,5-dimethoxy-benzamide (328039-93-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2.98 g / tetrahydrofuran / 2 h / 20 °C

2.1: NaN₃; NaI / dimethylformamide / 15 h / 75 - 80 °C

3.1: 1.85 g / SnCl₂; Et₃N; PhSH / tetrahydrofuran / 0.5 h / 20 °C

4.1: polymer-bound EDC / CHCl₃ / 6 h / 20 °C

4.2: 48.2 percent / acidic ion exchange resin P-SO₃H / CHCl₃ / 5 h

With sodium azide; polymer-bound EDC; thiophenol; triethylamine; sodium iodide; tin(ll) chloride; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(02)00207-9

Reference yield:

(3-azido-propyl)-(1-cyclohexylmethyl-piperidin-4-yl)-carbamic acid tert-butyl ester → 4-benzyloxy-N-[3-(1-cyclohexylmethyl-piperidin-4-ylamino)-propyl]-3,5-dimethoxy-benzamide (328039-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1.85 g / SnCl₂; Et₃N; PhSH / tetrahydrofuran / 0.5 h / 20 °C

2.1: polymer-bound EDC / CHCl₃ / 6 h / 20 °C

2.2: 48.2 percent / acidic ion exchange resin P-SO₃H / CHCl₃ / 5 h

With polymer-bound EDC; thiophenol; triethylamine; tin(ll) chloride; In tetrahydrofuran; chloroform;

DOI:10.1016/S0968-0896(02)00207-9

upstream raw materials:

4-(benzyloxy)-3,5-dimethoxybenzoic acid

(3-amino-propyl)-(1-cyclohexylmethyl-piperidin-4-yl)-carbamic acid tert-butyl ester

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