Dichloromethane → HCID 86734172, compound

HRID 1730161Notes

Reaction equation

Cl[O-].[Na+].[CH3:4][C:5]1([CH3:28])[C@@H:9]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH2:8][C@H:7]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)[NH:6]1.C(Cl)[Cl:30]>O>[Cl:30][N:6]1[C@@H:7]([C:16]2[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=2)[CH2:8][C@H:9]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:5]1([CH3:28])[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

30 Ml. of sodium hypochlorite (Cl2 = 10%) are added to a solution of 5.1 g. of 4-[trans-2,2-dimethyl-5-(3,4,5-trimethoxyphenyl)-3-pyrrolidinyl]-pyridine in 50 ml. of CH2Cl2. While stirring, the reaction mixture is heated at 50° C. for 2 hours. 10 Ml. of sodium hypochlorite are added and the reaction mixture is left to react for 2 more hours. After a further addition of 10 ml. of sodium hypochlorite and an additional 2 hours, the reaction mixture is treated with water and extracted three times with methylene chloride. The organic phase which results is washed with water, dried over sodium sulfate and evaporated under reduced pressure to yield crude 4-[trans-1-chloro-2,2-dimethyl-5-(3,4,5-trimethoxyphenyl)-3-pyrrolidinyl]-pyridine.

Workup

waitthe reaction mixture is left
customto react for 2 more hours
additionAfter a further addition of 10 ml
extractionextracted three times with methylene chloride
customThe organic phase which results
washis washed with water
dry with materialdried over sodium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-5862db4f2221464b9ea97cd5cceea227
Source dataset: uspto-grants-1976_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03991197

Reaction notes

Loading…