Water → Tert-butyl 4-(6-bromopyridin-3-yl)-1,4-diazepane-1-carboxylate

HRID 2182270

Reaction equation

HRID 2182270 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]2)[CH:2]=1.[Br:21]N1C(=O)CCC1=O.O>C(#N)C>[Br:21][C:6]1[N:1]=[CH:2][C:3]([N:7]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 108024941-(Pyridin-3-yl)-4-tert-butoxycarbonylhomopiperazine

Product 1

HCID 22478562Tert-butyl 4-(6-bromopyridin-3-yl)-1,4-diazepane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

1-(3-Pyridyl)-4-tert-butoxycarbonyl homopiperazine (25.0 g, 90.1 mmol) was solved in acetonitrile (400 ml) and cooled to 0° C. N-Bromosuccinimide (19.3 g, 108.2 mmol) was added during 10 min. Water (400 ml) was added and the mixture was extracted twice with diethyl ether (200 ml). Chromatography on silica gel with a mixture of petroleum: ethyl acetate (1:1) gave the title compound as free base. Yield 18.7 g, 58%.

Workup

  1. extractionthe mixture was extracted twice with diethyl ether (200 ml)
  2. additionChromatography on silica gel with a mixture of petroleum: ethyl acetate (1:1)

Sources & evidence

ORD record
ord-ef958457bc004d1daadb6440c6752247
Source dataset
uspto-grants-2005_05
Patent number
US06897219B2

Linked notes

Loading…