Isopropyl isocyanate → N-Isopropyl-4,4-dimethyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydro-isoquinoline-2(1H)-carboxamide

HRID 445286Notes

Reaction equation

HRID 445286 reaction equation
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[NH:4][CH2:3]1.[CH:23]([N:26]=[C:27]=[O:28])([CH3:25])[CH3:24]>ClCCCl>[CH:23]([NH:26][C:27]([N:4]1[CH2:3][C:2]([CH3:22])([CH3:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][CH:13]=1)=[O:28])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 595363404,4-Dimethyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59536349N-Isopropyl-4,4-dimethyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydro-isoquinoline-2(1H)-carboxamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A 25-mL round-bottomed flask was charged with 4,4-dimethyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (366 mg, 1.2 mmol), iso-propyl isocyanate (141 μL, 1.4 mmol), DCE (5 mL) and stirred at RT for 1 h. Then the solvent was removed under vacuum and the product was purified by recrystallization from a mixture of ether/hexane. MS (ESI, positive ion) m/z: 391 (M+H).

Workup

  1. customThen the solvent was removed under vacuum
  2. customthe product was purified by recrystallization from a mixture of ether/hexane

Sources & evidence

ORD record
ord-46b150e65acd4ab088ec059847856604
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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