Water → tert-Butyl 4-{[(2-nitrophenyl)methyl]amino}piperidine-1-carboxylate

HRID 1172283Notes

Reaction equation

HRID 1172283 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10].[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.O>C(Cl)Cl>[N+:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][NH:12][CH:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 77569alpha-Bromo-2-nitrotolueneHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 13046886tert-Butyl 4-{[(2-nitrophenyl)methyl]amino}piperidine-1-carboxylateYield 117.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(bromomethyl)-2-nitrobenzene (13.2 g, 61 mmol) in DCM (60 ml) was added dropwise to a solution of tert-butyl 4-aminopiperidine-1-carboxylate (14.6 g, 73 mmol) and TEA (13.4 ml, 91 mmol) in DCM (100 ml), followed by stirring the reaction mixture for a further 16 hours. The reaction mixture was then poured into water, and the layers separated. The aqueous layer was then extracted with DCM (2×). The organic layers were combined, washed with water (2×), brine, dried (MgSO4) and evaporated to dryness. The residue was taken up in EtOAc and filtered through a large plug of silica. The silica was washed with EtOAc until TLC analysis show no further material was eluting. Evaporation gave the product as an orange oil (24 g, 74%). LC/MS (10% to 99%): M/Z (M+H)+ (obs)=336; tR=2.23.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was then extracted with DCM (2×)
  3. washwashed with water (2×), brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. filtrationfiltered through a large plug of silica
  7. washThe silica was washed with EtOAc until TLC analysis show no further material
  8. washwas eluting
  9. customEvaporation

Sources & evidence

ORD record
ord-3edafeccb931432b90476479a0c2740b
Source dataset
uspto-grants-2010_11
Patent number
US07834000B2

Reaction notes

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