3-Isocyanatobenzonitrile → HCID 9827316, compound

HRID 1813962Notes

Reaction equation

HRID 1813962 reaction equation
[NH2:1][CH:2]([CH:10]([OH:26])[CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:27]([C:29]1[CH:30]=[C:31]([N:35]=[C:36]=[O:37])[CH:32]=[CH:33][CH:34]=1)#[N:28]>C1COCC1>[C:27]([C:29]1[CH:30]=[C:31]([NH:35][C:36]([NH:1][CH:2]([CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:10]([OH:26])[CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:16][CH2:17]2)=[O:37])[CH:32]=[CH:33][CH:34]=1)#[N:28]

Participants

4

Reactant 2

HCID 27333153-IsocyanatobenzonitrileHCID 22351223HCID 22351223, compound

Product 1

HCID 9827316HCID 9827316, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4-[4-(4-fluorophenyl)methyl-1-piperidinyl]-1-phenyl-butan-3-ol (50 mg, 0.14 mmoles) in 2.5 mL of dry THF was added 3-cyanophenyl isocyanate (20.2 mg, 0.14 mmoles) and the mixture was stirred for 15 minutes at room temperature. Then the solvent was evaporated off to give an oily residue. It was purified by column chromatography on silica gel with elution by EtOAc to give pure titled compound as an amorphous solid. MS (ES+) for C30H33FN4O2: 501.

Workup

  1. customThen the solvent was evaporated off
  2. customto give an oily residue
  3. customIt was purified by column chromatography on silica gel with elution by EtOAc

Sources & evidence

ORD record
ord-e64776125d2c456ca310187a34ec839b
Source dataset
uspto-grants-2005_04
Patent number
US06875776B2

Reaction notes

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