Water → 3-Chloro-12-cyclohexyl-5-[2-(piperidin-1-yl)ethyl]-5,6,7,12-tetrahydro-benzo[2,3]azepino[4,5-b]indole-9-carboxylic acid

HRID 1012284Notes

Reaction equation

HRID 1012284 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:12]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[C:13]4[C:18]([C:10]=3[CH2:9][CH2:8][N:7]([CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[C:6]=2[CH:38]=1)=[CH:17][C:16]([C:19]([O:21]CC)=[O:20])=[CH:15][CH:14]=4.[OH-].[Na+].[OH-].[Li+].O>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:12]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[C:13]4[C:18]([C:10]=3[CH2:9][CH2:8][N:7]([CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[C:6]=2[CH:38]=1)=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=4

Participants

7

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 23152627HCID 23152627, compound

Product 1

HCID 231523053-Chloro-12-cyclohexyl-5-[2-(piperidin-1-yl)ethyl]-5,6,7,12-tetrahydro-benzo[2,3]azepino[4,5-b]indole-9-carboxylic acidYield 72.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 3-chloro-12-cyclohexyl-5-[2-(piperidin-1-yl)ethyl]-5,6,7,12-tetrahydrobenzo[2,3]azepino[4,5-b]indole-9-carboxylate (309 mg, 0.579 mmol) in tetrahydrofuran (4 ml) and methanol (4 ml) was added 1N aqueous sodium hydroxide solution (2 ml), and the mixture was stirred at 70° C. for 2 hr. The mixture was allowed to cool to room temperature, 4N aqueous lithium hydroxide solution (2 ml) was added, and the mixture was stirred at 70° C. for 2 hr. The mixture was allowed to cool to room temperature, water (100 ml) was added, and the mixture was extracted with ethyl acetate (20 ml) and ether (10 ml). The aqueous layer was adjusted to pH 7 with 1N hydrochloric acid, and the precipitated solid was collected by filtration. The obtained solid was washed with water and dried in vacuo to give 3-chloro-12-cyclohexyl-5-[2-(piperidin-1-yl)ethyl]-5,6,7,12-tetrahydro-benzo[2,3]azepino[4,5-b]indole-9-carboxylic acid (212 mg, yield 72%).

Workup

  1. temperatureto cool to room temperature
  2. stirringthe mixture was stirred at 70° C. for 2 hr
  3. temperatureto cool to room temperature
  4. extractionthe mixture was extracted with ethyl acetate (20 ml) and ether (10 ml)
  5. filtrationthe precipitated solid was collected by filtration
  6. washThe obtained solid was washed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-f83e9696f4da400fb6f7e4dc088573f0
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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