Diisopropylethylamine → [1-(4-Cyano-3,5-difluoro-phenyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 2054891Notes

Reaction equation

HRID 2054891 reaction equation
[F:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].[CH3:12][C:13]([O:16][C:17]([NH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:18])([CH3:15])[CH3:14].C(N(CC)C(C)C)(C)C>CO>[C:13]([O:16][C:17](=[O:18])[NH:19][CH:20]1[CH2:25][CH2:24][N:23]([C:8]2[CH:9]=[C:2]([F:1])[C:3]([C:4]#[N:5])=[C:6]([F:11])[CH:7]=2)[CH2:22][CH2:21]1)([CH3:15])([CH3:12])[CH3:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 7371772,4,6-Trifluorobenzonitrile

Product 1

HCID 21090459[1-(4-Cyano-3,5-difluoro-phenyl)-piperidin-4-yl]-carbamic acid tert-butyl esterYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.0 g (6.4 mmol) of 2,4,6-trifluorobenzonitrile in MeOH (25 mL) was added 1.3 g (6.5 mmol) of 4-N-boc-amino-piperidine along with 1.2 mL (6.7 mmol) of N,N-diisopropylethylamine. The mixture was stirred at room temperature for 3 days then concentrated under reduced pressure to provide a white solid. The solid was washed with large amounts of H2O and dried under vacuum. The solid was recrystallized from hexane/EtOAc to provide 1.23 g (56%) of [1-(4-cyano-3,5-difluoro-phenyl)-piperidin-4-yl]-carbamic acid tert-butyl ester as a white solid.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customto provide a white solid
  3. washThe solid was washed with large amounts of H2O
  4. customdried under vacuum
  5. customThe solid was recrystallized from hexane/EtOAc

Sources & evidence

ORD record
ord-354f30b5f2d14e83890ae2334c1f962e
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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