Hydrochloric Acid → HCID 22444742, compound

HRID 964982Notes

Reaction equation

HRID 964982 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17][CH:16]3[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#N.[C:33](=O)([O-])[O-].[NH4+:37].[NH4+:38].[ClH:39]>C(O)C>[ClH:39].[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17][CH:16]3[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)(=[NH:38])[NH2:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 22444726HCID 22444726, compound

Product 1

HCID 22444742HCID 22444742, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

550 mg of methyl 4 -[4 -(4 -cyanophenyl)-1-piperazinyl]-1-ethoxycarbonylmethyl-3-piperidinepropionate was dissolved in 20 ml of ethanol, into which hydrogen chloride was made to blow 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 500 mg of ethyl 4-[4-(4-amidinophenyl)-1-piperazinyl]-1-ethoxycarbonylmethyl-3-piperidinepropionate hydrochloride.

Workup

  1. customto blow at from -10° C. to -20° C. until saturation
  2. customremoved 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-08970ba4ab944292a6786c5a05be016c
Source dataset
uspto-grants-1998_06
Patent number
US05773442

Reaction notes

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