Water → HCID 71294786, compound

HRID 1774694Notes

Reaction equation

HRID 1774694 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]4[CH:30]=[C:29]5[C:24]([CH:25]=[CH:26][C:27](=[O:31])[NH:28]5)=[CH:23][CH:22]=4)[CH2:12][CH2:11]3)=[CH:7][CH:8]=[CH:9][C:2]1=2.C(N(CC)CC)C.[CH:39]1([C:45](Cl)=[O:46])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.O>ClCCl>[CH:39]1([C:45]([O:31][C:27]2[CH:26]=[CH:25][C:24]3[C:29](=[CH:30][C:21]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][N:13]4[CH2:12][CH2:11][N:10]([C:6]5[C:3]6[CH:4]=[CH:5][S:1][C:2]=6[CH:9]=[CH:8][CH:7]=5)[CH2:15][CH2:14]4)=[CH:22][CH:23]=3)[N:28]=2)=[O:46])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 11978813Brexpiprazole

Product 1

HCID 71294786HCID 71294786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)-butoxy]-1H-quinolin-2-one (800 mg) synthesized in the same manner as in WO2006/112464 (Example 1) in dichloromethane (20 ml) was added triethylamine (0.64 ml), with stirring under ice-cooling, cyclohexanecarbonyl chloride (0.49 ml) was added and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=4:1) to give 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)-butoxy]-quinolin-2-yl cyclohexanecarboxylate (1.08 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=4:1)

Sources & evidence

ORD record
ord-d87db847dba240299c60b03b6f8bd7f0
Source dataset
uspto-grants-2016_02
Patent number
US09260420B2

Reaction notes

Loading…