2-Chlorocyclohexanone → HCID 25006717, compound

HRID 1443920Notes

Reaction equation

HRID 1443920 reaction equation
Cl.[CH3:2][C:3]([CH3:19])([CH3:18])[CH2:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH2:13][CH2:12][CH2:11]2)=[O:6].Cl[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22]1=O>C(O)C>[CH:17]1[C:8]([NH:7][C:5](=[O:6])[CH2:4][C:3]([CH3:19])([CH3:18])[CH3:2])=[CH:9][C:10]2[CH2:11][CH2:12][CH2:13][N:14]3[C:15]=2[C:16]=1[C:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=13

Participants

4

Reactant 2

HCID 132032-ChlorocyclohexanoneHCID 68685534HCID 68685534, compound

Product 1

HCID 25006717HCID 25006717, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3,3-dimethyl-N-1,2,3,4-tetrahydroquinolin-6-ylbutanamide hydrochloride (50 mg, 0.18 mmol) and 2-chlorocyclohexanone (28 mg, 0.21 mmol) in ethanol (2.5 mL) was heated in a microwave to 150° C. for 50 min. The reaction mixture was concentrated and the crude material was purified by flash column chromatography (elution with 20% ethyl acetate-hexane) to provide N-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-2-yl-3,3-dimethylbutanamide (19 mg). MS (ESI) m/z 325; HPLC purity major: no impurities are detected at 210-370 nm window; and no impurities are detected at 252 nm (max. abs), RT=10.8 (Xterra RP18, 3.5 u, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN and MeOH) for 10 min, hold 4 min).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude material was purified by flash column chromatography (elution with 20% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-d3cadf7078404632b62ce19bd7ba0414
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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