Methane → Domperidone

HRID 1833683Notes

Reaction equation

HRID 1833683 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH:31][CH:32]([CH:36]([OH:40])[C:37]([O-:39])=[O:38])[C:33]([O-:35])=[O:34].C>O>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH2:31].[OH:31][CH:32]([CH:36]([OH:40])[C:37]([OH:39])=[O:38])[C:33]([OH:35])=[O:34]

Participants

6

Reactant 3

HCID 297MethaneHCID 3151DomperidoneHCID 38061142,3-Dihydroxybutanedioate

Product 2

HCID 3151DomperidoneYield 85.3%HCID 22042229HCID 22042229, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.2 parts of 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one are converted into the (+)-2,3-dihydroxybutanedioate salt in 100 parts of water at reflux temperature. The solution is treated for 10 minutes with a mixture of 0.5 parts of activated charcoal and 0.2 parts of hyflo. The latter is filtered off over hyflo and the filtrate is cooled till an oily precipitate is formed. The oily product solidifies upon heating for a while. The whole is allowed to cool to room temperature and stirred for 3 hours at this temperature. The product is filtered off, washed with water and dried in vacuo for 18 hours at 60° C, yielding 10.24 parts (85.3%) of 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemi-[R-(R*,R*)](+)-2,3-dihydroxybutanedioate hydrate; mp. 184.1° C; [α] = + 5.13° (c = 1% CH3OH).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe latter is filtered off over hyflo
  3. temperaturethe filtrate is cooled till an oily precipitate
  4. customis formed
  5. temperatureupon heating for a while
  6. filtrationThe product is filtered off
  7. washwashed with water
  8. customdried in vacuo for 18 hours at 60° C

Sources & evidence

ORD record
ord-4ff482c3aceb454a92473580f188b109
Source dataset
uspto-grants-1978_01
Patent number
US04066772

Reaction notes

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