Hydrochloric Acid → Batanopride Hydrochloride

HRID 1382962Notes

Reaction equation

HRID 1382962 reaction equation
C([N+](CCCC)(CCCC)CCCC)CCC.[NH2:18][C:19]1[C:34]([Cl:35])=[CH:33][C:22]([C:23]([NH:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[O:24])=[C:21]([OH:36])[CH:20]=1.Cl[CH:38]([CH3:42])[C:39](=[O:41])[CH3:40].Cl>C(#N)C>[ClH:35].[NH2:18][C:19]1[C:34]([Cl:35])=[CH:33][C:22]([C:23]([NH:25][CH2:26][CH2:27][N:28]([CH2:29][CH3:30])[CH2:31][CH3:32])=[O:24])=[C:21]([O:36][CH:38]([CH3:42])[C:39](=[O:41])[CH3:40])[CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 16028TetrabutylammoniumHCID 200263-Chloro-2-butanoneHCID 9817332o-Desmethyl metoclopramide

Product 1

HCID 59691Batanopride Hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the tetra-n-butylammonium salt of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (0.53 g, 1.0 mmole) in acetonitrile (6 ml) was treated with 3-chloro-2-butanone (0.11 ml, 0.12 g, 1.1 mmole) and stirred at 20° for 16 hours. After removal of the acetonitrile at reduced pressure, the residue was treated with 10 ml water and extracted with ethyl acetate. The extracts were washed with dilute sodium carbonate, dried and concentrated to leave an oil which was converted to a monohydrochloride salt with 1.0 ml 1N hydrochloric acid. Crystallization of this salt from 2-propanol-ethyl acetate gave the title compound, mp. 176°-179°. This material was identical to that prepared in Example 7C.

Workup

  1. customAfter removal of the acetonitrile at reduced pressure
  2. additionthe residue was treated with 10 ml water
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with dilute sodium carbonate
  5. customdried
  6. concentrationconcentrated
  7. customto leave an oil which
  8. customCrystallization of this salt from 2-propanol-ethyl acetate

Sources & evidence

ORD record
ord-74584300215748aeb7a7e44a92f7622b
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Reaction notes

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