N-bromobutanimide → tert-Butyl 4-(4-amino-3-bromophenyl)-piperidine-1-carboxylate

HRID 1992032Notes

Reaction equation

HRID 1992032 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:28])C(=O)C1>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([Br:28])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

Product 1

HCID 56834849tert-Butyl 4-(4-amino-3-bromophenyl)-piperidine-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.00 g (7.24 mmol) 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (as prepared in the previous step) in 40 mL of CH3CN was treated with solid 1.25 g (7.02 mmol) NBS and stirred at RT for 15 min. The solvents were evaporated in vacuo, the residue was taken up in EtOAc (70 mL) and washed with saturated aqueous NaHCO3 (2×50 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue with 10-25% EtOAc-hexanes afforded 3.12 g (97%) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C12H16N2O2Br, 299.0 (M−C4H9+2H), found 299.1/301.1.

Workup

  1. customThe solvents were evaporated in vacuo
  2. washwashed with saturated aqueous NaHCO3 (2×50 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-172f91f300e141f1995e83aa734ebc60
Source dataset
uspto-grants-2010_01
Patent number
US07645755B2

Reaction notes

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