N-bromobutanimide → HCID 58179516, compound

HRID 254001Notes

Reaction equation

HRID 254001 reaction equation
[Br:1]N1C(=O)CCC1=O.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[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.C([O-])(O)=O.[Na+]>CC#N>[Br:1][C:13]1[S:9][C:10]([CH:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 58179661HCID 58179661, compound

Product 1

HCID 58179516HCID 58179516, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Bromosuccinimide (4.9 g, 28.08 mmol) was added in portions to a solution of tert-butyl 4-(thiophen-2-yl)piperidine-1-carboxylate (5.0 g, 18.72 mmol) in MeCN at −10° C. The reaction mixture was stirred for 30 minutes and treated with sat. aq. NaHCO3 solution. The mixture was extracted with CH2Cl2 and the organics washed with water and brine solution, dried (Na2SO4), filtered, and evaporated to obtain crude product. Purification by silica gel chromatography (2% EtOAc/pet ether) yielded tert-Butyl 4-(5-bromothiophen-2-yl)piperidine-1-carboxylate (1.5 g, 21% from tert-butyl 4-hydroxy-4-(thiophen-2-yl)piperidine-1-carboxylate); 1H-NMR (400 MHz, CHCl3): 6.85 (d, 1H), 6.58 (d, 1H), 4.22-4.10 (d, 2H), 3.90-3.78 (m, 3H), 1.98-1.90 (d, 2H), 1.65-1.48 (m, 2H), 1.45 (s, 9H); ES-MS: 346.3, 348.3 (M+H).

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. washthe organics washed with water and brine solution
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto obtain crude product
  7. customPurification by silica gel chromatography (2% EtOAc/pet ether)

Sources & evidence

ORD record
ord-72d3189113234c09a22d0ea5b221e946
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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