dibenzoyl-L(+)tartaric acid → HCID 131720733, compound

HRID 964981Notes

Reaction equation

HRID 964981 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C@H:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17][C@H:16]3[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[C:33]([C@@:41]([C:56]([OH:58])=[O:57])([OH:55])[C@@:42]([C:47](=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([OH:46])[C:43]([OH:45])=[O:44])(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(OCC)(=O)C.C(OC(C)C)(C)C>[C:47]([C@:42]([C:43]([OH:45])=[O:44])([OH:46])[C@:41]([C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([OH:55])[C:56]([OH:58])=[O:57])(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C@H:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17][C@H:16]3[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:13][CH2:14]2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 12362976dibenzoyl-L(+)tartaric acidHCID 131720734HCID 131720734, compound

Product 1

HCID 131720733HCID 131720733, compoundYield 5.6%

Reagents, catalysts & solvents 1

HCID 22281796Diisopropylether ethyl acetateSolvent

Procedure

6.3 g of (+/-)-cis-diethyl 4-[4-(4-cyanophenyl)-1-piperazinyl]-1,3-piperidinediacetate and 5.4 g of (-)-dibenzoyl-L-tartaric acid were dissolved in 180 ml of a mixed solvent of ethyl acetate/diisopropyl ether (1/1) and subjected to resolving crystallization. The crystals obtained were recrystallized several times from a mixed solvent of ethyl acetate/diisopropyl ether (1/1), whereby was obtained 640 mg of (-)-cis-diethyl 4-[4-(4-cyanophenyl)-1-piperazinyl]-1,3-piperidinediacetate (-)-dibenzoyl-D-tartrate (98.4% e.e.).

Workup

  1. customcrystallization
  2. customThe crystals obtained
  3. customwere recrystallized several times from a mixed solvent of ethyl acetate/diisopropyl ether (1/1)

Sources & evidence

ORD record
ord-9b963dd42586437596e3bfc52cc0e531
Source dataset
uspto-grants-1998_06
Patent number
US05773442

Reaction notes

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