Hydrochloric Acid → 1-(3-(10,11-Dihydro-5h-dibenzo[b,f]azepin-5-yl)-1-propyl)-3-pyrrolidinacetic acid

HRID 1378418Notes

Reaction equation

HRID 1378418 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][N:13]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][CH2:16][C:15]3[CH:24]=[CH:25][CH:26]=[CH:27][C:14]2=3)[CH2:6]1.[OH-].[Na+].Cl>C(O)C>[CH:24]1[C:15]2[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:13]([CH2:12][CH2:11][CH2:10][N:7]3[CH2:8][CH2:9][CH:5]([CH2:4][C:3]([OH:28])=[O:2])[CH2:6]3)[C:14]=2[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 536769941-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propyl)-3-pyrrolidinacetic acid methyl ester

Product 1

HCID 187993221-(3-(10,11-Dihydro-5h-dibenzo[b,f]azepin-5-yl)-1-propyl)-3-pyrrolidinacetic acidYield 5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (0.85 g, 0.0022 mol) was dissolved in ethanol (6 ml) and 0.5N NaOH was added. By continued addition of 0.25N NaOH pH was kept at approximately 12 for 3 days. Dilute HCl (approx. 1N) was added until pH=7, and the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel (50 g) using a mixture of dichloromethane, methanol and acetic acid (20:2:1) as eluent. The product fractions were stripped with dichloromethane, affording 0.04 g (3.8%) of 1-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propyl)-3-pyrrolidinacetic acid as an amorphous product.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was purified by column chromatography on silica gel (50 g)
  3. additiona mixture of dichloromethane, methanol and acetic acid (20:2:1) as eluent

Sources & evidence

ORD record
ord-ed374707492847b494e0b773ff7a3c98
Source dataset
uspto-grants-1997_09
Patent number
US05668129

Reaction notes

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