Hydrochloric Acid → 13-cyclohexyl-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

HRID 1394848Notes

Reaction equation

HRID 1394848 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:25]([O:27]C)=[O:26])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]=[CH:18][C:17]4[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-].Cl>C1COCC1.CO.O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:25]([OH:27])=[O:26])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]=[CH:18][C:17]4[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11667856methyl 13-cyclohexyl-7H-indolo[2,1-a][2]benzazepine-10-carboxylate

Product 1

HCID 1161739113-cyclohexyl-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acidYield 91%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 1 (371 mg, 1 mmol) in THF (4 mL), methanol (3 mL), and 1.7M LiOH (3 mL, 5.1 mmol) was stirred at reflux for 1.5 hours. The mixture was cooled to room temperature, diluted with water, and acidified with dilute HCl. The resulting precipitate was collected by filtration, washed with cold water, and dried to provide 324 mg of the desired product (91% yield). ESI-MS m/z 358 (MH+); 1H NMR (300 MHz, DMSO-d6) 1.37-2.05 (m, 10H), 2.78 (m, 1H), 4.06 (s, 1H), 5.17 (s, 1H), 6.39 (m, 1H), 6.89 (d, J=10.61 Hz, 1H), 7.50 (m, 4H), 7.60 (m, 1H), 7.88 (d, J=8.78 Hz, 1H), 8.24 (s, 1H), 12.59, (s, 1H).

Workup

  1. temperatureat reflux for 1.5 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with cold water
  4. customdried

Sources & evidence

ORD record
ord-d9dd3248177c492fb82132fb38200324
Source dataset
uspto-grants-2008_03
Patent number
US07348425B2

Reaction notes

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