1,2-Dichloroethane → N-[2-[4-(4-Indolyl)-1-piperazinyl]ethyl]-N-(2-pyridyl)cyclohexanecarboxamide HCL

HRID 1603683Notes

Reaction equation

HRID 1603683 reaction equation
[CH:1]([CH2:3][N:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])=O.[NH:19]1[C:27]2[C:22](=[C:23]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+].[Cl:54]CCCl>O.C(O)(=O)C>[ClH:54].[NH:19]1[C:27]2[C:22](=[C:23]([N:28]3[CH2:33][CH2:32][N:31]([CH2:1][CH2:3][N:4]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=4)[C:5]([CH:7]4[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]4)=[O:6])[CH2:30][CH2:29]3)[CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 10340Sodium CarbonateHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 5049666Sodium triacetoxyborohydrideHCID 21713921N-Formylmethyl-N-(2-pyridyl)cyclohexanecarboxamide

Product 1

HCID 69821352N-[2-[4-(4-Indolyl)-1-piperazinyl]ethyl]-N-(2-pyridyl)cyclohexanecarboxamide HCL

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 0.94 g of N-formylmethyl-N-(2-pyridyl)cyclohexanecarboxamide, 0.69 g of 1-(4-indolyl)piperazine, 1.21 g of sodium triacetoxyborohydride, 0.44 ml of acetic acid and 30 ml of 1,2-dichloroethane was stirred at room temperature for 3 h. Afterwards, it was diluted with 20 ml of water and alkalinized to pH=10 with 20% Na2CO3. The aqueous layer was extracted twice with 1,2-dichloroethane and the combined organic layers were dried (sodium sulfate) and evaporated to dryness in vacuo affording a crude which was purified by flash chromatography (methylene chloride-methanol 98:2 to 95:5) affording 0.96 g of the title compound as a base. This was dissolved in 40 ml of methylene chloride and to the solution was added 3.8 N hydrogen chloride in diethyl ether. The precipitated title compound was filtered, yielding 0.66 g. M.p. 181-7° C.

Workup

  1. extractionThe aqueous layer was extracted twice with 1,2-dichloroethane
  2. dry with materialthe combined organic layers were dried (sodium sulfate)
  3. customevaporated to dryness in vacuo
  4. customaffording a crude which
  5. customwas purified by flash chromatography (methylene chloride-methanol 98:2 to 95:5)

Sources & evidence

ORD record
ord-49d5e3e9720a4aecbec97284cf210cd9
Source dataset
uspto-grants-1999_11
Patent number
US05990114

Reaction notes

Loading…