Citric Acid → HCID 19031546, compound

HRID 266880Notes

Reaction equation

HRID 266880 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[Cl:14][C:15]1[CH:16]=[C:17]([C:22]2([CH:26]([OH:35])[CH2:27][S:28][CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])[CH2:25][CH2:24][CH2:23]2)[CH:18]=[CH:19][C:20]=1[Cl:21]>C(O)C.CCOCC>[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[Cl:14][C:15]1[CH:16]=[C:17]([C:22]2([CH:26]([OH:35])[CH2:27][S:28][CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])[CH2:25][CH2:24][CH2:23]2)[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

5

Reactant 2

HCID 311Citric AcidHCID 9841901HCID 9841901, compound

Product 1

HCID 19031546HCID 19031546, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of citric acid (1.73 g) in hot ethanol (10 ml) was added to a solution of (+)-1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-[3-(dimethylamino) propylthio]ethanol (3.29 g, preparation described in Example 16) in ether (30 ml) and the mixture was stored at 4° C. for 18 hours. The resulting solid was collected by filtration, washed with ether and dried in vacuo at ambient temperature for 24 hours, to give (+)-1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-[3-(dimethylamino)-propylthio]ethanol citrate as a white solid (3.8 g) , m.p. 109°-115° C., [α]rtD =+10.88° (C=1; methanol).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with ether
  3. customdried in vacuo at ambient temperature for 24 hours

Sources & evidence

ORD record
ord-70c42b35f6844f3d97107f4830760a0b
Source dataset
uspto-grants-1997_07
Patent number
US05652271

Reaction notes

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