Triethylamine → Tert-butyl 3-((2-bromo-5-nitropyridin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 384655Notes

Reaction equation

HRID 384655 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[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][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]2)[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27564831-Boc-3-(aminomethyl)piperidineHCID 596134182-Bromo-4-chloro-5-nitropyridine

Product 1

HCID 59613413Tert-butyl 3-((2-bromo-5-nitropyridin-4-ylamino)methyl)piperidine-1-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 3-(aminomethyl)-1-boc-piperidine (409 mg, 1.91 mmol) in acetonitrile (2.5 mL) was added dropwise to a solution of 2-bromo-4-chloro-5-nitropyridine (431 mg, 1.82 mmol) and triethylamine (0.28 mL, 2.0 mmol) in acetonitrile (10 mL). The solution was stirred for 1 hr 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 3-((2-bromo-5-nitropyridin-4-ylamino)methyl)piperidine-1-carboxylate as a yellow-brown solid (718 mg, 95%) 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-4e8e897bb47d49bdb2b63a5b39c7bbf0
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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