N-bromobutanimide → HCID 24752432, compound

HRID 2246469Notes

Reaction equation

HRID 2246469 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[CH2:4][N:5]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:6]2.[Br:17]N1C(=O)CCC1=O>C(#N)C>[Br:17][C:14]1[N:13]=[CH:12][C:11]([N:5]2[CH2:6][CH:7]3[N:2]([CH3:1])[CH:3]([CH2:10][CH2:9][CH2:8]3)[CH2:4]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 24752137HCID 24752137, compound

Product 1

HCID 24752432HCID 24752432, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 9-methyl-3-pyridin-3-yl-3,9-diaza-bicyclo[3.3.1]nonane (1.38, 6.2 mmol) and acetonitrile (40 ml) was cooled to 0° C. N-bromo-succinimide (1.1 g, 6.2 mmol) in acetonitrile (20 ml) was added during 2 h. The mixture was stirred over night at room-temperature. The mixture was evaporated. Aqueous sodium hydroxide (20 ml, 1 M) was added followed by extraction with dichloromethane (3×10 ml). The product was purified by silica gel column chromatography using a solvent mixture of dichloromethane, methanol and aqueous ammonia (9:1:1%). Yield 900 mg (49%). LC-ESI-HRMS of [M+H]+ shows 296.0757 Da. Calc. 296.076235 Da, dev. −1.8 ppm.

Workup

  1. customThe mixture was evaporated
  2. additionAqueous sodium hydroxide (20 ml, 1 M) was added
  3. extractionfollowed by extraction with dichloromethane (3×10 ml)
  4. customThe product was purified by silica gel column chromatography
  5. additiona solvent mixture of dichloromethane, methanol and aqueous ammonia (9:1:1%)

Sources & evidence

ORD record
ord-beee0db63e21486489d639cb0cb2d8db
Source dataset
uspto-grants-2010_03
Patent number
US07687523B2

Reaction notes

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