HCID 10452317, compound → 4-(3-Cyclopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxymethyl)-benzoic acid

HRID 645818Notes

Reaction equation

HRID 645818 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:27]=[CH:26][C:15]3[CH2:16][CH2:17][N:18]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:19][CH2:20][C:14]=3[CH:13]=2)=[CH:6][CH:5]=1>CO.[OH-].[Na+].O>[CH:21]1([N:18]2[CH2:19][CH2:20][C:14]3[CH:13]=[C:12]([O:11][CH2:10][C:7]4[CH:8]=[CH:9][C:4]([C:3]([OH:28])=[O:2])=[CH:5][CH:6]=4)[CH:27]=[CH:26][C:15]=3[CH2:16][CH2:17]2)[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 1

HCID 10452317HCID 10452317, compound

Product 1

HCID 103614874-(3-Cyclopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxymethyl)-benzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

4-(3-Cyclopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxymethyl)-benzoic acid methyl ester (E88) (3.1 g, 8.1 mmol)) was dissolved in a mixture of methanol (90 ml), 2N sodium hydroxide (12 ml) and water (30 ml). The resulting mixture was stirred at 60° C. for 4 hours and then cooled to room temperature. The mixture was concentrated in vacuo to remove the organic solvents and then acidified to pH 6 (2N hydrochloric acid). The resulting precipitates were filtered, washed with water and dried under vacuum to afford the title compound (E89); MS (ES+) m/e 366 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. customto remove the organic solvents
  4. customThe resulting precipitates
  5. filtrationwere filtered
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-bff041ae6e804096b648db2a6d0f1311
Source dataset
uspto-grants-2010_04
Patent number
US07704994B2

Reaction notes

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