Phenyl isocyanate → HCID 58997134, compound

HRID 1592552Notes

Reaction equation

HRID 1592552 reaction equation
[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:16][C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:24]1([N:30]=[C:31]=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[C:24]1([NH:30][C:31]([N:13]2[CH2:14][CH2:15][CH:10]([N:9]([CH2:16][C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:8][C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[CH2:11][CH2:12]2)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 58996965Bis-(3-methyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine

Product 1

HCID 58997134HCID 58997134, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.), stirred solution of COMPOUND 249 (66 mg, 0.21 mmol) in CH2Cl2 (2 mL) was added phenyl isocyanate (30 μL, 0.28 mmol). After 15 minutes, the cooling bath was removed and the reaction mixture was warmed to room temperature. After an additional 45 minutes, the mixture was concentrated under reduced pressure. Purification of the crude material by radial chromatography on silica gel (1 mm plate, 25:1:1 CH2Cl2-MeOH—NH4OH) provided 84 mg (84%) of COMPOUND 270 as a white solid. 1H NMR (CDCl3) δ 1.62-1.78 (m, 2H), 1.95-1.99 (m, 2H), 2.09 (s, 6H), 2.68-2.79 (m, 3H), 3.83 (s, 4H), 4.14 (d, 2H, J=13.5 Hz), 6.39 (br s, 1H), 6.99-7.12 (m, 3H), 7.25-7.39 (m, 6H), 8.34 (d, 2H, J=3.6 Hz); 13C NMR (CDCl3) δ 18.39, 27.45, 44.86, 54.98, 57.83, 120.41, 122.86, 123.17, 129.13, 133.86, 138.50, 139.80, 146.23, 155.40, 157.50; ES-MS m/z 430 (M+H). Anal. Calcd. For C26H31N5O.0.5CH2Cl2: C, 67.43; H, 6.83; N, 14.84. Found: C, 67.77; H, 6.99; N, 14.90.

Workup

  1. customthe cooling bath was removed
  2. waitAfter an additional 45 minutes
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customPurification of the crude material by radial chromatography on silica gel (1 mm plate, 25:1:1 CH2Cl2-MeOH—NH4OH)

Sources & evidence

ORD record
ord-ee90451a40bb40068f7b3a262738b0b8
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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