2-Bromophenyl isocyanate → 4-(2-Bromophenylcarbamoyloxy)piperidine-1-carboxylic Acid tert-Butyl Ester

HRID 1097815Notes

Reaction equation

HRID 1097815 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[O:10].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>CN(C)C=O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([O:24][C:9](=[O:10])[NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 1370972-Bromophenyl isocyanateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 597071934-(2-Bromophenylcarbamoyloxy)piperidine-1-carboxylic Acid tert-Butyl EsterYield 103.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-Bromophenyl isocyanate (10.2 g, 51.5 mmol) was dissolved in N,N-dimethylformamide (40 mL) with 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (10.36 g, 51.5 mmol). The reaction mixture was stirred at 50° C. for 20 hours before being concentrated under reduced pressure. The crude was taken up in dichloromethane (200 mL) and washed with water (2×150 mL) and brine (1×150 mL). The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound as a light yellow oil (21.36 g). MS m/z: [M+H+] calcd for C17H23BrN2O4 399-08; found 399.3.

Workup

  1. concentrationbefore being concentrated under reduced pressure
  2. washwashed with water (2×150 mL) and brine (1×150 mL)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-294e56d8e5c14bd69dfe1c3c6c70af52
Source dataset
uspto-grants-2012_03
Patent number
US08143277B2

Reaction notes

Loading…