16413-75-5

Usage

InChI:InChI=1/C12H17NO2/c1-9(13(3)10(2)14)12(15)11-7-5-4-6-8-11/h4-9,12,15H,1-3H3

Synthetic route

ephedrine hydrochloride (63991-26-4) + acetic anhydride (108-24-7) → 1-(Phenyl)-2-(N-methyl-N-acetylamino)-1-propanol (16413-75-5)

Conditions	Yield
With sodium carbonate In water at 10℃; for 2h;	79%

α-bromo-β--α-phenyl-propane → 1-(Phenyl)-2-(N-methyl-N-acetylamino)-1-propanol (16413-75-5)

Conditions	Yield
With silver nitrate

N-(2-bromo-1-methyl-2-phenyl-ethyl)-N-methyl-acetamide + silver nitrate → 1-(Phenyl)-2-(N-methyl-N-acetylamino)-1-propanol (16413-75-5)

Conditions	Yield
dextrorotatory α-bromo-β-acetylmethylamino-α-phenyl-propane;

1-(Phenyl)-2-(N-methyl-N-acetylamino)-1-propanol (16413-75-5) → α-(N-Methyl-N-acetylamino)propiophenone (73082-23-2)

Conditions	Yield
With sodium hypochlorite In acetic acid at 20℃; for 2h;	57%

1-(Phenyl)-2-(N-methyl-N-acetylamino)-1-propanol (16413-75-5) + methyl iodide (74-88-4) → pseudoephedrine (90-82-4)

Conditions	Yield
at 100℃;

1-(Phenyl)-2-(N-methyl-N-acetylamino)-1-propanol (16413-75-5) → methcathinone (5650-44-2, 28521-94-0, 112117-24-5)

Conditions	Yield
With manganese(IV) oxide; oxonium Yield given. Multistep reaction;

1-(Phenyl)-2-(N-methyl-N-acetylamino)-1-propanol (16413-75-5) + hydrochloric acid (25 percent ) → d-pseudoephedrine hydrochloride

1-(Phenyl)-2-(N-methyl-N-acetylamino)-1-propanol (16413-75-5) → methylamino-2-methylamino-1-phenyl-1-propane (14594-86-6, 124871-06-3, 124871-07-4, 130857-96-4, 130857-97-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) MnO2; 2) H3O(+) 2: NaBH3CN / methanol / 72 h / Ambient temperature View Scheme

1-(Phenyl)-2-(N-methyl-N-acetylamino)-1-propanol (16413-75-5) → methylamino-2-methylamino-1-phenyl-1-propane (14594-86-6, 124871-06-3, 124871-07-4, 130857-96-4, 130857-97-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) MnO2; 2) H3O(+) 2: NaBH3CN / methanol / 72 h / Ambient temperature View Scheme

Upstream product

• 63991-26-4 ephedrine hydrochloride 
• 108-24-7 acetic anhydride 
• 90-82-4 rac-pseudoephedrine 
• 29724-89-8 N-((1RS,2RS)-2-chloro-1-methyl-2-phenyl-ethyl)-N-methyl-acetamide 
• 90-81-3 ephedrine 
• 1630-34-8 (1RS:2SR)-2-methylamino-1-acetoxy-1-phenyl-propane; hydrochloride 

Downstream Products

• 5650-44-2 methcathinone 
• 73082-23-2 α-(N-Methyl-N-acetylamino)propiophenone 
• 14594-86-6 methylamino-2-methylamino-1-phenyl-1-propane 
• 14594-86-6 methylamino-2-methylamino-1-phenyl-1-propane 
• 90-82-4 pseudoephedrine 

Relevant academic research and scientific papers

MISE EN EVIDENCE PAR RMN-(1)H ET -(13)C D'ISOMERISME Z/E ET D'EQUILIBRE CONFORMATIONNEL SUR UNE SERIE DE DERIVES MONO- ET DIACETYLES DE 2-ALKYLAMINO-1-PHENYLPROPAN-1-OLS

(1)H- and (13)C NMR studies of mono- and diacetylated-erythro- and threo-2-alkylamino-1-phenylpropan-1-ols, C6H5CHOHCHNHRCH3 (R = H, CH3, C2H5 AND i-C3H7) show that the series exhibit Z/E isomerism about the C-N amide bond.The Z/E ratio increases in the monoacetylated series CH3 1-C2 and N-C2 bonds.In the Z configuration, the conformer Z-s-syn where the proton H-2 is syn with the N-alkyl substituent predominates.