Carbon Dioxide → HCID 66758895, compound

HRID 556908Notes

Reaction equation

HRID 556908 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:15][C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[CH:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)[CH2:7][C:6]=2[CH:32]=1.CCCCCC.C([Li])CCC.[C:44](=[O:46])=[O:45]>C1COCC1>[C:44]([C:2]1[CH:3]=[CH:4][C:5]2[O:15][C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[CH:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)[CH2:7][C:6]=2[CH:32]=1)([OH:46])=[O:45]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 66758102HCID 66758102, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 66758895HCID 66758895, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[3-(8-Bromo-5,11-dihydro[1]benzoxepino[2,3-b]pyridin-5-ylidene)propyl]-4-(4-chlorophenyl)piperidine (Example 160) (130 mg) in THF (1.0 ml) was added 1.6M n-butyllithium hexane solution (0.17 ml) at −78° C. After stirring 10 minutes at the same temperature, CO2 (dry-ice) was added to the mixture. After being warmed to ambient temperature, the mixture was stirred for 30 minutes at the same temperature. The mixture was concentrated in vacuo. The resulting oil was purified by silica gel chromatography eluted with dichloromethane-methanol (5:1) to give the titled compound

Workup

  1. additionwas added to the mixture
  2. concentrationThe mixture was concentrated in vacuo
  3. customThe resulting oil was purified by silica gel chromatography
  4. washeluted with dichloromethane-methanol (5:1)

Sources & evidence

ORD record
ord-f32905eaaf844efa82f5775ba60814cd
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

Loading…