Acetic Acid → tert-Butyl 4-{[2-(2-nitrophenyl)ethyl]amino}piperidine-1-carboxylate

HRID 1695887Notes

Reaction equation

HRID 1695887 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][NH2:12])([O-:3])=[O:2].O=[C:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][NH:12][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 124981232-Nitrophenethylamine

Product 1

HCID 18444265tert-Butyl 4-{[2-(2-nitrophenyl)ethyl]amino}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 2-(2-nitrophenyl)ethanamine (4 g, 24 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (4.8 g, 24 mmol) in MeOH (48 ml) was brought to pH 5 by the addition of acetic acid. NaBH3CN (2.3 g, 36 mmol) was added and the reaction mixture was stirred at RT for 3 hours. The solvent was evaporated and the residue was taken up in EtOAc and sat. aq. Na2CO3. The layers were separated and the organic layer was washed with brine, dried (Na2SO4) and evaporated to dryness. Purification by column chromatography (0% to 7% MeOH in DCM) gave the desired product. LC/MS (10% to 99%): M/Z (M+H)+ (obs)=350; tR=2.22.

Workup

  1. customThe solvent was evaporated
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customPurification by column chromatography (0% to 7% MeOH in DCM)

Sources & evidence

ORD record
ord-6b270c62602146568205e6c1e01973c1
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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