Hydrochloric Acid → HCID 178522241, compound

HRID 572230Notes

Reaction equation

HRID 572230 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1.Cl.[NH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]1.CCN(CC)CC.Cl>CN(C=O)C.O>[OH:23][C@H:20]1[CH2:21][CH2:22][C@H:17]([NH:16][C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:9][CH:8]=2)=[O:12])[CH2:18][CH2:19]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 178479278HCID 178479278, compound

Product 1

HCID 178522241HCID 178522241, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(trifluoromethoxy)phenyl isocyanate (2 g, 9.8 mmol) in DMF (100 mL) were added trans-4-aminocyclohexanol hydrochloride (1.6 g, 10.8 mmol) and Et3N (1.5 mL, 10.8 mmol) at 0° C. The reaction mixture was warmed up to room temperature and stirred overnight. After adding aq 1N HCl (20 mL) and water (100 mL), the resulting white precipitates were collected by suction filtration. The collected solid was thoroughly washed with water. Recrystallization from acetone at −78° C. afforded 2.4 g (70%) of the title compound as a white solid. mp 224.1-225.3° C. 1H NMR (300 MHz, DMSO-d6; δ 8.50 (s, 1H), 7.45 (d, J=9 Hz, 2H), 7.21 (d, J=9 Hz, 2H), 6.06 (d, J=8 Hz, 1H), 4.55 (d, J=4 Hz, 1H), 3.44-3.33 (m, 2H), 1.91-1.68 (m, 4H), 1.31-1.07 (m, 4H).

Workup

  1. customthe resulting white precipitates
  2. filtrationwere collected by suction filtration
  3. washThe collected solid was thoroughly washed with water
  4. customRecrystallization from acetone at −78° C.

Sources & evidence

ORD record
ord-a16880cb6c0044139f569120a4c0f7ed
Source dataset
uspto-grants-2015_05
Patent number
US09029401B2

Reaction notes

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