Acetic Acid → HCID 178511578, compound

HRID 2364691Notes

Reaction equation

HRID 2364691 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]1[CH2:14][CH2:13][C@@H:12]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH:22]3[CH2:24][CH2:23]3)[CH2:17][CH2:16]2)[CH2:11][CH2:10]1)C1C=CC=CC=1.C(O)(=O)C.[H][H].[O-2].[Al+3].[O-2].[O-2].[Al+3]>ClCCl.CO.[Pd]>[CH:22]1([CH2:21][N:18]2[CH2:19][CH2:20][N:15]([C@@H:12]3[CH2:13][CH2:14][C@H:9]([NH2:8])[CH2:10][CH2:11]3)[CH2:16][CH2:17]2)[CH2:23][CH2:24]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 9989226AluminaHCID 178418361HCID 178418361, compoundHCID 178420351HCID 178420351, compound

Product 1

HCID 178511578HCID 178511578, compoundYield 172%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(cis)-N,N-Dibenzyl-4-[4-(cyclopropylmethyl)piperazin-1-yl]cyclohexanamine 12d (2.44 g, 5.83 mmol) was dissolved in 30 mL mixture solvent of dichloromethane and methanol (V/V=1:2) followed by the addition of palladium/carbon (1.22 g, 10%) and 0.1 mL acetic acid, filled with hydrogen three times. The reaction mixture was reacted at 3 atmosphere for 12 hours. The resulting solution was added with 4 g alkaline aluminum oxide (200-300 mesh) and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (cis)-4-[4-(cyclopropylmethyl)piperazin-1-yl]cyclohexanamine 12e (2.38 g, yield: 98.0%) as a colorless solid.

Workup

  1. customThe reaction mixture was reacted at 3 atmosphere for 12 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-06bb9baa81c3446586c75033b32b299d
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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