Dichloromethane → tert-Butyl (3R)-3-(aminomethyl)-4-benzylpiperazine-1-carboxylate

HRID 1685116Notes

Reaction equation

HRID 1685116 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@H:9]1[CH2:21][N:22]1C(=O)C2C(=CC=CC=2)C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.O.NN>C(O)C>[NH2:22][CH2:21][C@H:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 67264804HCID 67264804, compound

Product 1

HCID 57415720tert-Butyl (3R)-3-(aminomethyl)-4-benzylpiperazine-1-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 200 mL round bottom flask was added 15R (6.66 g, 15.3 mmol) and 110 mL of 10:1 dichloromethane:ethanol. Hydrazine hydrate (7.66 g, 10 equiv.) was added and the reaction was heated to reflux for three hours. The precipitate which had formed was removed by filtration through Celite. The filtrate was concentrated under high vacuum and temperature (to remove hydrazine). The residue was resuspended in dichloromethane and the resultant precipitate was removed by filtration through a Buchner funnel. The filtrate was concentrated to leave a clear oil 15S (3.27 g, 73%) which was analytically pure.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for three hours
  3. customThe precipitate which had formed
  4. customwas removed by filtration through Celite
  5. concentrationThe filtrate was concentrated under high vacuum and temperature (to remove hydrazine)
  6. customthe resultant precipitate was removed by filtration through a Buchner funnel
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-dfaa9e2cb3aa4bb79d06315ad6085ea2
Source dataset
uspto-grants-2012_04
Patent number
US08148367B2

Reaction notes

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