Hydrochloric Acid → HCID 131720735, compound

HRID 964985Notes

Reaction equation

HRID 964985 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([C@](C([O-])=O)(O)[C@](C(=O)C1C=CC=CC=1)(O)C([O-])=O)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[NH4+:63].[NH4+].[ClH:65]>C(O)C>[ClH:65].[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)(=[NH:63])[NH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 131720737HCID 131720737, compound

Product 1

HCID 131720735HCID 131720735, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

660 mg of (+)-cis-diethyl 4-[4-(4-cyanophenyl)-1-piperazinyl]-1,3-piperidinediacetate-(+)-dibenzoyl-D-tartrate was dissolved in 20 ml of ethanol, into which hydrogen chloride was bubbled at from -10° C. to -20° C. until saturation. This was heated up to room temperature and stirred overnight, and thereafter the solvent was removed by distillation. The residue thus obtained was dissolved in 20 ml of ethanol, and 1.0 g of ammonium carbonate was added thereto and stirred at room temperature overnight. The solvent was removed from the reaction mixture by distillation, and the resulting residue was purified by silica gel column chromatography (using an eluent of chloroform/methanol=10/1) to obtain 300 mg of (+)-cis-diethyl 4-[4-(4-amidinophenyl)-1-piperazinyl]-1,3-piperidinediacetate hydrochloride.

Workup

  1. customwas bubbled at from -10° C. to -20° C. until saturation
  2. customthe solvent was removed by distillation
  3. customThe residue thus obtained
  4. stirringstirred at room temperature overnight
  5. customThe solvent was removed from the reaction mixture by distillation
  6. customthe resulting residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-087f179958554fe3af85f5d8a06fb041
Source dataset
uspto-grants-1998_06
Patent number
US05773442

Reaction notes

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