3-Isocyanatobenzonitrile → HCID 9827316, compound

HRID 1060723Notes

Reaction equation

HRID 1060723 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-935d7537e818485fb2296066a785c049
Source dataset
uspto-grants-2003_02
Patent number
US06525069B1

Reaction notes

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