Triethylamine → tert-Butyl 3-(aminomethyl)-4-methylpiperazine-1-carboxylate

HRID 624537Notes

Reaction equation

HRID 624537 reaction equation
[C:1]([CH:3]1[N:8]([CH3:9])[CH2:7][CH2:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4]1)#[N:2].C(N(CC)CC)C>CO.[Ni]>[NH2:2][CH2:1][CH:3]1[N:8]([CH3:9])[CH2:7][CH2:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 84689957HCID 84689957, compound

Product 1

HCID 77474534tert-Butyl 3-(aminomethyl)-4-methylpiperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 3-cyano-4-methylpiperazine-1-carboxylate, prepared as described in Step A, (10.5 g, 47 mmol) in methanol (200 mL) was added metallic nickel (10 g) and triethylamine (5 mL). The mixture was stirred at ambient temperature overnight under atmosphere of hydrogen gas (50 psi). Upon consumption of tert-butyl 3-cyano-4-methylpiperazine-1-carboxylate, the mixture was filtered, and the filtrate was concentrated under vacuum to provide crude tert-butyl 3-(aminomethyl)-4-methylpiperazine-1-carboxylate used in the next step without purification.

Workup

  1. customUpon consumption of tert-butyl 3-cyano-4-methylpiperazine-1-carboxylate
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-442f2223a8604285bf2b96bd8c52ea07
Source dataset
uspto-grants-2016_04
Patent number
US09303041B2

Reaction notes

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