Benzoyl chloride → 1-[(4aRS,8SR,8aRS)-4-benzoyl-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-2-(3,4-dichlorophenyl)ethan-1-one

HRID 1876805Notes

Reaction equation

HRID 1876805 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH:21]3[CH:16]([CH2:17][CH2:18][CH2:19][CH:20]3[N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[NH:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[C:27]([N:15]1[CH:16]2[CH:21]([CH:20]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH2:19][CH2:18][CH2:17]2)[N:12]([C:10](=[O:11])[CH2:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:13][CH2:14]1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 687760732-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one

Product 1

HCID 687823131-[(4aRS,8SR,8aRS)-4-benzoyl-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-2-(3,4-dichlorophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2, 2-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one (111 mg, 0.28 mmol) was dissolved in absolute CH2Cl2 (14 ml) and benzoyl chloride (47 mg, 0.35 mmol) was added dropwise. The mixture was stirred at room temperature overnight and then evaporated in vacuo. The residue was purified by flash chromatography (Ø 2 cm, CH2Cl2/MeOH/NH3 9.5:0.5:0.05, l=15 cm, V=5 ml) and was obtained as a yellowish resin.

Workup

  1. customevaporated in vacuo
  2. customThe residue was purified by flash chromatography (Ø 2 cm, CH2Cl2/MeOH/NH3 9.5:0.5:0.05, l=15 cm, V=5 ml)
  3. customwas obtained as a yellowish resin

Sources & evidence

ORD record
ord-aab9c25987654d43a4f59de68e96f7b0
Source dataset
uspto-grants-2012_11
Patent number
US08309725B2

Reaction notes

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