1-Benzylpiperazine → 1-[n-Cyclohexylcarbonyl-n-(2-pyridyl)-2-aminoethyl]-4-benzylpiperazine

HRID 649814Notes

Reaction equation

HRID 649814 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:2].[CH2:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:32](O[BH-](OC(=O)C)OC(=O)C)(=[O:34])C.[Na+].[C:46](=O)([O-])O.[Na+]>O.C(Cl)Cl.C(O)(=O)C>[CH3:46][O:2][CH:1]([O:34][CH3:32])[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].[CH:7]1([C:5]([N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:3][CH2:1][N:29]2[CH2:30][CH2:31][N:26]([CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:27][CH2:28]2)=[O:6])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

9

Reactant 4

HCID 759941-BenzylpiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21713921N-Formylmethyl-N-(2-pyridyl)cyclohexanecarboxamide

Product 2

HCID 217139081-[n-Cyclohexylcarbonyl-n-(2-pyridyl)-2-aminoethyl]-4-benzylpiperazineHCID 21713913N-[(2,2-Dimethoxy)ethyl]-N-(2-pyridyl)cyclohexanecarboxamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.3 g of Compound 1B, 0.2 mL of 1-benzylpiperazine, 0.14 mL of acetic acid, 0.38 g of sodium triacetoxyborohydride and 7 mL of methylene chloride was stirred at room temperature for 24 h. Afterwards, it was diluted with water, alkalinized with 5% aq. sodium hydrogencarbonate. The organic layer was separated, dried on sodium sulphate and evaporated to dryness in vacuo affording a crude, which was purified by flash chromatography (methylene chloride—methanol 9.5:0.5) affording 0.03 g (3.6% overall from Compound 1A) of the title product.

Workup

  1. customThe organic layer was separated
  2. customdried on sodium sulphate
  3. customevaporated to dryness in vacuo
  4. customaffording a crude, which
  5. customwas purified by flash chromatography (methylene chloride—methanol 9.5:0.5)

Sources & evidence

ORD record
ord-09f50e0090264b51b724b89b75e78105
Source dataset
uspto-grants-2001_08
Patent number
US06271234B1

Reaction notes

Loading…