2-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1) → HCID 86744794, compound

HRID 2051401Notes

Reaction equation

HRID 2051401 reaction equation
O.[C:2]([OH:14])(=[O:13])[CH2:3][C:4]([CH2:9][C:10]([OH:12])=[O:11])([C:6]([OH:8])=[O:7])[OH:5].[OH:15][C:16]1[C:21]([O:22][CH3:23])=[CH:20][C:19](/[CH:24]=[CH:25]/[CH:26]=[CH:27]/[C:28]([NH:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][CH:36]([C:39]3[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[NH:41][CH:40]=3)[CH2:35][CH2:34]2)=[O:29])=[CH:18][C:17]=1[O:48][CH3:49]>O.C(O)C>[C:2]([OH:14])(=[O:13])[CH2:3][C:4]([CH2:9][C:10]([OH:12])=[O:11])([C:6]([OH:8])=[O:7])[OH:5].[OH:15][C:16]1[C:17]([O:48][CH3:49])=[CH:18][C:19](/[CH:24]=[CH:25]/[CH:26]=[CH:27]/[C:28]([NH:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][CH:36]([C:39]3[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[NH:41][CH:40]=3)[CH2:35][CH2:34]2)=[O:29])=[CH:20][C:21]=1[O:22][CH3:23]

Participants

5

Reactant 2

HCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 10412674HCID 10412674, compound

Product 1

HCID 86744794HCID 86744794, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

To a hot solution of citric acid hydrate (2.65 g) in a mixture of water and ethanol (4:6, V/V, 50 ml) was added 1-[2-{5-(4-hydroxy-3, 5-dimethoxyphenyl)-(2E, 4E)-2, 4pentadienoylamino}ethyl]-4-(3-indolyl)piperidine (6.0 g), and then a mixture of water and ethanol (4:6, V/V, 50 ml) was added thereto. The mixture was stirred for 6 hours at ambient temperature, and the resulting precipitate was collected by filtration. The residue was washed with a mixture of water and ethanol, and dried to give 1-[2-{5-(4-hydroxy-3, 5-dimethoxyphenyl)-(2E, 4E)-2, 4pentadienoylamino}ethyl]-4-[3-indolyl)piperidine citrate (7.2 g).

Workup

  1. additionwas added
  2. filtrationthe resulting precipitate was collected by filtration
  3. washThe residue was washed with a mixture of water and ethanol
  4. customdried

Sources & evidence

ORD record
ord-31a4cab47d224aa79caaf790c05fe8b3
Source dataset
uspto-grants-1991_05
Patent number
US05017703

Reaction notes

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