(2S)-N,N-dibenzyl-3-[4-(cyclopropylmethyl)piperazin-1-yl]-2-methoxy-propan-1-amine → (2S)-3-[4-(cyclopropylmethyl)piperazin-1-yl]-2-methoxy-propan-1-amine

HRID 2364743Notes

Reaction equation

HRID 2364743 reaction equation
C([N:8](CC1C=CC=CC=1)[CH2:9][C@H:10]([O:22][CH3:23])[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH:19]2[CH2:21][CH2:20]2)[CH2:14][CH2:13]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH:19]1([CH2:18][N:15]2[CH2:14][CH2:13][N:12]([CH2:11][C@@H:10]([O:22][CH3:23])[CH2:9][NH2:8])[CH2:17][CH2:16]2)[CH2:20][CH2:21]1

Participants

5

Reactant 2

HCID 68107689(2S)-N,N-dibenzyl-3-[4-(cyclopropylmethyl)piperazin-1-yl]-2-methoxy-propan-1-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 68107823(2S)-3-[4-(cyclopropylmethyl)piperazin-1-yl]-2-methoxy-propan-1-amineYield 106.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2S)—N,N-Dibenzyl-3-[4-(cyclopropylmethyl)piperazin-1-yl]-2-methoxy-propan-1-amine 35c (500 mg, 1.23 mmol) was dissolved in 30 mL of methanol followed by the addition of palladium/carbon (100 mg, 10%), filled with hydrogen for three times. The reaction mixture was stirred at room temperature for 12 hours and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound (2S)-3-[4-(cyclopropylmethyl)piperazin-1-yl]-2-methoxy-propan-1-amine 35d (299 mg) as a yellow oil liquid, which was used in the next step without further furification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cb4d02aaa0ea4dbbbd898dcde2ebbbcd
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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