Benzoyl isocyanate → HCID 21465540, compound

HRID 1939984Notes

Reaction equation

HRID 1939984 reaction equation
[C:1]([N:9]=[C:10]=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1>ClCCl>[C:2]1([C:1]([NH:9][C:10]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)=[O:11])=[O:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 21465540HCID 21465540, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-bath cooled solution of benzoyl isocyanate (7.725 ml, 0.0525 Mol) in dichloromethane (400 ml) was added 4-amino-1-benzyl piperidine (10 g, 10.72 ml, 0.0525 Mol) dropwise. When the addition was complete the solution was allowed to stir at room temperature for 1 h then the solvent was removed by rotary evaporation. The residue was triturated with diethyl ether and collected by filtration to give the required product as a white solid 15.4 g (87%). Mp. 179°-180° C. 1H NMR (DMSO) δ 1.51 (2H, m), 1.86 (2H, m), 2.14 (2H, m), 2.69 (2H, m), 3.47 (2H, s), 3.65 (1H, m), 7.24-7.33 (5H, m), 7.50 (2H, t, J=7.9 Hz), 7.61 (1H, t, J=7.9 Hz), 7.96 (2H, d, J=7.9 Hz), 8.69 (1H, d, J=7.8 Hz), 10.67 (1H, br s); MS (CI) m/e 338 [MH]+. Anal. Found C, 70.99; H, 6.86; N, 12.41. C20H23N3O2 requires C, 71.19; H, 6.87; N, 12.45%.

Workup

  1. additionWhen the addition
  2. customthe solvent was removed by rotary evaporation
  3. customThe residue was triturated with diethyl ether
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a0d19501e5024db4893696abf4f711f1
Source dataset
uspto-grants-1997_12
Patent number
US05698573

Reaction notes

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