Hydrogen Bromide → Acetamide, N-[2-[(4-chlorophenyl)methyl]-4-piperidinyl]-, trans-

HRID 1738917Notes

Reaction equation

HRID 1738917 reaction equation
Br.COC([N:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13](=[O:15])[CH3:14])[CH2:8][C@H:7]1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=O.O>C(O)(=O)C>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][C@@H:7]2[CH2:8][C@@H:9]([NH:12][C:13](=[O:15])[CH3:14])[CH2:10][CH2:11][NH:6]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 544394991-Piperidinecarboxylic acid, 4-(acetylamino)-2-[(4-chlorophenyl)methyl]-, methyl ester, trans-

Product 1

HCID 54566395Acetamide, N-[2-[(4-chlorophenyl)methyl]-4-piperidinyl]-, trans-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

51.8 ml of 33% hydrogen bromide in acetic acid are added to (2R*,4S*)-4-acetylamino-2-(4-chloro-benzyl)-piperidine-1-carboxylic acid methyl ester (30.0 g, 92.3 mmol). After 16 hours, 200 ml of water are added to the mixture which is then washed twice with toluene. The aqueous phase is rendered basic and extracted twice with ethyl acetate. The organic phases are dried on potassium carbonate and concentrated by evaporation using a rotary evaporator. The title compound crystallises in the form of a hydrochloride from EtOH/ethyl acetate. M.p.: 288-289° C. TLC: methylene chloride/methanol/conc. ammonia (90:9:1) Rf =0.17, FD-MS: (M+1)+ =267.

Workup

  1. washis then washed twice with toluene
  2. extractionextracted twice with ethyl acetate
  3. customThe organic phases are dried on potassium carbonate
  4. concentrationconcentrated by evaporation
  5. customa rotary evaporator
  6. customThe title compound crystallises in the form of a hydrochloride from EtOH/ethyl acetate

Sources & evidence

ORD record
ord-b04b2a0ca3f94e6bbc7b549594789db9
Source dataset
uspto-grants-1999_10
Patent number
US05965562

Reaction notes

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