Phenyl isocyanate → 41220-40-0

HRID 2396475Notes

Reaction equation

HRID 2396475 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1.C(N(CC)CC)C>ClCCl>[CH2:17]([N:14]1[CH2:15][CH2:16][CH:11]([NH:10][C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:9])[CH2:12][CH2:13]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 406434241220-40-0Yield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.14 ml (10.5 mmol) of phenyl isocyanate are slowly added dropwise to a solution of 1.90 g (10.0 mmol) of 4-amino-1-benzylpiperidine and 1.46 ml (10.5 mmol) of triethylamine in 40 ml of dichloromethane. The reaction mixture may subsequently be stirred at room temperature for 1 h, and is then evaporated to dryness in vacuo. The residue is mixed with 50 ml of diethyl ether, stirred well, separated off by filtration, washed with 5 ml of diethyl ether and dried in a high vacuum. 2.62 g (85%) of the title compound are obtained as colourless crystals.

Workup

  1. customis then evaporated to dryness in vacuo
  2. additionThe residue is mixed with 50 ml of diethyl ether
  3. stirringstirred well
  4. customseparated off by filtration
  5. washwashed with 5 ml of diethyl ether
  6. customdried in a high vacuum

Sources & evidence

ORD record
ord-5e7758224c304f92ae55acf4c612ccd5
Source dataset
uspto-grants-1996_02
Patent number
US05492918

Reaction notes

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