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

HRID 1584755Notes

Reaction equation

HRID 1584755 reaction equation
[C:1]([NH:4][C@H:5]1[CH2:10][CH2:9][N:8](C(OC)=O)[C@H:7]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:6]1)(=[O:3])[CH3:2].Br.O>C(O)(=O)C>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][C@@H:7]2[CH2:6][C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:10][CH2:9][NH:8]2)=[CH:21][CH:20]=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

Methyl (2R*,4S*)-4-acetylamino-2-(4-chlorobenzyl)piperidine-1-carboxylate (30.0 g, 92.3 mmol) are treated with 51.8 ml 33% strength hydrogen bromide in acetic acid. After 16 hours, the mixture is treated with 200 ml of water and 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 evaporated on a rotary evaporator. The title compound crystallizes from EtOHI ethyl acetate as the hydrochloride. M.p.: 288-289° C. TLC: methylene chloride/methanolconc. ammonia (90:9:1) Rf =0.17, FD-MS: (M+1)+ =267.

Workup

  1. washwashed twice with toluene
  2. extractionextracted twice with ethyl acetate
  3. customThe organic phases are dried on potassium carbonate
  4. customevaporated on a rotary evaporator
  5. customThe title compound crystallizes from EtOHI ethyl acetate as the hydrochloride

Sources & evidence

ORD record
ord-cc8070cebec14dceb1184da75609ffd7
Source dataset
uspto-grants-1999_08
Patent number
US05935951

Reaction notes

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