Borane;tetrahydrofuran → Tert-butyl 3-((pyridin-3-ylamino)methyl)piperazine-1-carboxylate

HRID 549770

Reaction equation

HRID 549770 reaction equation
B.C1COCC1.[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([CH:16]2[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)=O)[CH:8]=1>C1COCC1>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][CH2:14][CH:16]2[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)[CH:8]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 59671553Tert-butyl 3-(pyridin-3-ylcarbamoyl)piperazine-1-carboxylate

Product 1

HCID 59671589Tert-butyl 3-((pyridin-3-ylamino)methyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-THF complex (1.0 M solution in THF, 3.4 mL, 3.4 mmol) was added to a solution of tert-butyl 3-(pyridin-3-ylcarbamoyl)piperazine-1-carboxylate (522 mg, 1.70 mmol) in THF (4 mL). The reaction mixture was heated to reflux for 5 h. Upon cooling to rt, the reaction mixture was carefully quenched by the dropwise addition of MeOH. After gas evolution ceased, MeOH (10 mL) was added, and the reaction mixture was heated to reflux overnight. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure, yielding the title compound which was used without further purification. LC-MS: RT=2.90 min, [M+H]+=293.1.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 h
  3. customthe reaction mixture was carefully quenched by the dropwise addition of MeOH
  4. additionMeOH (10 mL) was added
  5. temperaturethe reaction mixture was heated
  6. temperatureto reflux overnight
  7. temperatureUpon cooling to rt
  8. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2134e578d1b34acb8e02faf082894561
Source dataset
uspto-grants-2011_05
Patent number
US07943622B2

Linked notes

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