Cyclohexanone, 3,3-dimethyl- → N-(3,3-dimethylcyclohexyl)-N'-(4-tert-butylcyclohexyl)-piperazine

HRID 2107612Notes

Reaction equation

HRID 2107612 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][C:18]1([CH3:25])[CH2:23][CH2:22][CH2:21][C:20](=O)[CH2:19]1.C([BH3-])#N.[Na+]>[Cl-].[Zn+2].[Cl-]>[CH3:17][C:18]1([CH3:25])[CH2:23][CH2:22][CH2:21][CH:20]([N:14]2[CH2:15][CH2:16][N:11]([CH:8]3[CH2:7][CH2:6][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10][CH2:9]3)[CH2:12][CH2:13]2)[CH2:19]1

Participants

5

Reactant 3

HCID 76322Cyclohexanone, 3,3-dimethyl-HCID 5003444Sodium cyanoborohydrideHCID 14553997N-(4-Tert-butylcyclohexyl)-piperazine

Product 1

HCID 14553998N-(3,3-dimethylcyclohexyl)-N'-(4-tert-butylcyclohexyl)-piperazine

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

5.0 g (22.3 millimoles) of N-(4-tert-butylcyclohexyl)-piperazine, 5.4 g (44.6 millimoles) of 3,3-dimethylcyclohexanone, 1.7 g (12.3 millimoles) of zinc(II) chloride and 1.6 g (24.5 millimoles) of sodium cyanoborohydride are stirred for 48 hours at 20° C. The mixture is evaporated down under reduced pressure, the residue is hydrolyzed with 1N sodium hydroxide solution and the mixture is extracted with methyl tert-butyl ether. Working up the organic extract in the usual manner gives 3.7 g (50% of theory) of a product in the form of white crystals (mp. 90°-92° C.; for IR data, see Table 1b).

Workup

  1. customThe mixture is evaporated down under reduced pressure
  2. extractionthe mixture is extracted with methyl tert-butyl ether
  3. extractionWorking up the organic extract in the usual manner
  4. customgives 3.7 g (50% of theory) of a product in the form of white crystals (mp. 90°-92° C.; for IR data, see Table 1b)

Sources & evidence

ORD record
ord-667ecded76b5452288c39e234ec080df
Source dataset
uspto-grants-1990_06
Patent number
US04935426

Reaction notes

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