Phenyl isocyanate → HCID 21936994, compound

HRID 1241886Notes

Reaction equation

HRID 1241886 reaction equation
[C:1]1([CH:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:8][CH2:9][N:10]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:36]1([N:42]=[C:43]=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>ClCCl>[C:30]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9][N:10]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:23])[F:22])[CH:15]=2)=[O:12])[CH:24]2[CH2:25][CH2:26][N:27]([C:43]([NH:42][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:44])[CH2:28][CH2:29]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 21936992HCID 21936992, compound

Product 1

HCID 21936994HCID 21936994, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(3,3-diphenylpropyl)-N-(4-piperidinyl)-N′-[3-(trifluoromethyl)phenyl]urea (24 mg, 0.05 mmol) is dissolved in dichloromethane. Phenylisocyanate (9 mg, 0.075 mmol, 1.5 eq.) is added and the mixture is agitated for 2.5 hours. The aminomethyl resin (0.02 mmol) is added and the reaction is again agitated overnight. The resin is filtered, rinsed with dichloromethane and the filtrate is concentrated. The oil obtained is passed through a silica gel cartridge eluting with an equimolar mixture of heptane and ethyl acetate in order to obtain 12 mg (yield=40%) of a yellow oil after concentration.

Workup

  1. waitthe reaction is again agitated overnight
  2. filtrationThe resin is filtered
  3. washrinsed with dichloromethane
  4. concentrationthe filtrate is concentrated
  5. customThe oil obtained
  6. washeluting with an equimolar mixture of heptane and ethyl acetate in order

Sources & evidence

ORD record
ord-5fcb50ab778f42f8b048a4e0d96111fd
Source dataset
uspto-grants-2006_10
Patent number
US07115634B2

Reaction notes

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