Triethylamine → Tert-butyl 4-((2-bromo-5-nitropyridin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 556791Notes

Reaction equation

HRID 556791 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[Br:16][C:17]1[CH:22]=[C:21](Cl)[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=1.C(N(CC)CC)C>C(#N)C>[Br:16][C:17]1[CH:22]=[C:21]([NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 596134182-Bromo-4-chloro-5-nitropyridine

Product 1

HCID 59613428Tert-butyl 4-((2-bromo-5-nitropyridin-4-ylamino)methyl)piperidine-1-carboxylateYield 98.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 4-(aminomethyl)-1-boc-piperidine (370 mg, 1.73 mmol) in acetonitrile (1 mL) was added over 1 minute to a solution of 2-bromo-4-chloro-5-nitropyridine (373 mg, 1.57 mmol) and triethylamine (0.24 mL, 1.73 mmol) in acetonitrile (5 mL). The solution was stirred for 30 minutes then partitioned between dichloromethane and water. The aqueous phase was extracted with dichloromethane (×3) and the combined organic phases were dried (Na2SO4) and concentrated to give tert-butyl 4-((2-bromo-5-nitropyridin-4-ylamino)methyl)piperidine-1-carboxylate as a light brown foam (640 mg, 98%) which was used without further purification.

Workup

  1. customthen partitioned between dichloromethane and water
  2. extractionThe aqueous phase was extracted with dichloromethane (×3)
  3. dry with materialthe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-19573565ed4d464db9205d5630e0de31
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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