Hydrochloric Acid → 1-(3-(10,11-Dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)4-piperidineacetic acid hydrochloride

HRID 1979042Notes

Reaction equation

HRID 1979042 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)[CH2:8][CH2:7]1)C.[ClH:31].O>C(O)C>[ClH:31].[CH:26]1[C:17]2[CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:15]([CH2:14][CH2:13][CH2:12][N:9]3[CH2:8][CH2:7][CH:6]([CH2:5][C:4]([OH:30])=[O:3])[CH2:11][CH2:10]3)[C:16]=2[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 543656911-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)4-piperidineacetic acid ethyl ester

Product 1

HCID 699488421-(3-(10,11-Dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)4-piperidineacetic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the above ester (0.6 g, 0.0015 mol) in ethanol (5 ml) 4 N sodium hydroxide (0.8 ml) was added and the mixture was stirred at room temperature for 2.5 h and then left in a freezer overnight. The cold reaction mixture was allowed to warm to room temperature during 1 h, and 4 N hydrochloric acid (1.2 ml) and water (10 ml) were added. The mixture was extracted with dichloromethane (2×100 ml). The combined organic extracts were dried (MgSO4) and the solvent was evaporated in vacuo. The residue was reevaporated with a mixture of acetone and isopropyl acetate and then treated with a mixture of acetone and isopropyl acetate to give a solid which was isolated and dried in vacuo. This afforded 0.33 g of the title compound.

Workup

  1. waitleft in a freezer overnight
  2. customThe cold reaction mixture
  3. temperatureto warm to room temperature during 1 h
  4. extractionThe mixture was extracted with dichloromethane (2×100 ml)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was reevaporated with a mixture of acetone and isopropyl acetate
  8. additiontreated with a mixture of acetone and isopropyl acetate
  9. customto give a solid which
  10. customwas isolated
  11. customdried in vacuo

Sources & evidence

ORD record
ord-d60303baad8649669ca572277696183f
Source dataset
uspto-grants-2001_05
Patent number
US06239148B1

Reaction notes

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