3-(Trifluoromethyl)phenyl isocyanate → HCID 10121014, compound

HRID 2267075Notes

Reaction equation

HRID 2267075 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:14]1([CH:20]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:21][CH2:22][NH:23][CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[C:33]([O:32][C:30]([N:27]1[CH2:26][CH2:25][CH:24]([N:23]([CH2:22][CH2:21][CH:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=2)=[O:11])[CH2:29][CH2:28]1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 21936984HCID 21936984, compound

Product 1

HCID 10121014HCID 10121014, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

246 mg (1.32 mmol) of 3-(trifluoromethyl)phenyl isocyanate is added to a solution of tert-butyl 4-[(3,3-diphenylpropyl)amino]-1-piperidine carboxylate (470 mg, 1.2 mmol) in 5 ml of dichloromethane. The solution is agitated for 45 minutes, and the aminomethyl resin (180 mg, 0.36 mmol) is added and the reaction medium is again placed on an orbital shaker for 45 minutes. The resin is filtered and washed with dichloromethane. The filtrate is concentrated in vacuo in order to produce 610 mg (yield=87%) of a white foam.

Workup

  1. waitthe reaction medium is again placed on an orbital shaker for 45 minutes
  2. filtrationThe resin is filtered
  3. washwashed with dichloromethane
  4. concentrationThe filtrate is concentrated in vacuo in order

Sources & evidence

ORD record
ord-948c25b908f54e8ea3f56d48bdd19fe4
Source dataset
uspto-grants-2010_12
Patent number
US07858789B2

Reaction notes

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