Tetrabutylammonium → HCID 14372559, compound

HRID 1382970Notes

Reaction equation

HRID 1382970 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.Br[CH2:38][CH2:39][CH2:40][N:41]1[C:45](=[O:46])[C:44]2=[CH:47][CH:48]=[CH:49][CH:50]=[C:43]2[C:42]1=[O:51]>C(#N)C>[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][CH2:38][CH2:39][CH2:40][N:41]2[C:45](=[O:46])[C:44]3=[CH:47][CH:48]=[CH:49][CH:50]=[C:43]3[C:42]2=[O:51])[CH:20]=1

Participants

5

Reactant 3

HCID 16028TetrabutylammoniumHCID 21611N-3-BromopropylphthalimideHCID 9817332o-Desmethyl metoclopramide

Product 1

HCID 14372559HCID 14372559, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of the tetra-n-butylammonium salt of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (15.8 g, 30 mmoles) (prepared in Preparation 3) in acetonitrile (50 ml) was added N-(3-bromopropyl)phthalimide and the mixture stirred for 16 hours at ambient temperature and 1 hour at 65°-70° C. This was concentrated in vacuo and the residue partitioned between water and a 1:1 mixture of ether and methylene chloride. The organic phase was washed several times with water, dried and concentrated to small volume causing crystallization. This was filtered and the solid washed with ether to give 12.3 g (86.7%) of the title product as white solid, mp. 141°-143°.

Workup

  1. concentrationThis was concentrated in vacuo
  2. customthe residue partitioned between water
  3. additiona 1:1 mixture of ether and methylene chloride
  4. washThe organic phase was washed several times with water
  5. customdried
  6. concentrationconcentrated to small volume
  7. customcrystallization
  8. filtrationThis was filtered
  9. washthe solid washed with ether

Sources & evidence

ORD record
ord-83d0aa30cfdc4aeaab1bfc48f57108aa
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Reaction notes

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