3-Isocyanatobenzonitrile → HCID 9827316, compound

HRID 1278709Notes

Reaction equation

HRID 1278709 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]-l-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-759daed9a11c4ea184ed36f84567ed1f
Source dataset
uspto-grants-2002_09
Patent number
US06444686B1

Reaction notes

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