Hydrochloric Acid → HCID 69646397, compound

HRID 1858703Notes

Reaction equation

HRID 1858703 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:13]([CH2:14][O:15][CH3:16])[CH2:12][N:11](C(OC(C)(C)C)=O)[CH:10](OC)[CH:9]2[C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)=[CH:4][CH:3]=1.[ClH:36].[CH3:37][OH:38]>C(Cl)Cl>[ClH:36].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH:13]([CH2:14][O:15][CH3:16])[CH2:12][N:11]([O:38][CH3:37])[CH2:10][CH:9]2[C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86604432HCID 86604432, compound

Product 1

HCID 69646397HCID 69646397, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 60 mg (0.11 mg) of tert-butyl (3RS,4RS,5SR)-4-(4-bromo-phenyl)-5-methoxymethyl-3-naphthalen-2-yl-methoxy-piperidine-1-carboxylate in 5 ml of methylene chloride was treated with 2 ml of 2N hydrogen chloride in methanol and stirred at room temperature for 2 hours. For the working-up, the reaction solution was evaporated under reduced pressure. The residue was recrystallized from diethyl ether and gave 53 mg (98% of theory) of (3RS,4RS,5SR)-4-(4-bromo-phenyl)-5-methoxymethyl-3-naphthalen-2-yl-methoxy-piperidine hydrochloride as a colourless solid; MS: 442 (M+H)+.

Workup

  1. customthe reaction solution was evaporated under reduced pressure
  2. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-26d79aa4996f43e082d7526c627f8121
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

Loading…