Dichloromethane → HCID 21481261, compound

HRID 917992Notes

Reaction equation

HRID 917992 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(Cl)Cl.[F:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:13]3[CH2:25][N:26]([CH2:28][CH2:29][CH2:30][CH:31]([C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=4)[OH:32])[CH2:27][C:12]=3[C:11]=2[CH:10]=1>N1C=CC=CC=1>[F:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:13]3[CH2:25][N:26]([CH2:28][CH2:29][CH2:30][CH:31]([C:33]4[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=4)[O:32][C:1](=[O:3])[CH3:2])[CH2:27][C:12]=3[C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 6367Acetyl chlorideHCID 12649801HCID 12649801, compound

Product 1

HCID 21481261HCID 21481261, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetyl chloride (260 mg., 3.3 m moles) in 10 ml. of methylene chloride is added dropwise to a cold solution of 959 mg. (2.2 m moles) of 7-fluoro-4-(p-fluorophenyl)-2-[4-(p-fluorophenyl)-4-hydroxybutyl]-1,2,3,4-tetrahydropyrrolo[3,4-b]indole in 30 ml. of methylene chloride containing 350 mg. (4.4 m moles) of pyridine. Following the addition, the reaction mixture is allowed to warm to room temperature and stir overnight. The mixture is decanted into a cold saturated aqueous sodium bicarbonate solution, and the crude product is extracted (3 × 50 ml.) with methylene chloride. The combined organic extracts are dried over magnesium sulfate and concentrated to an oil, which on chromatographing on a silica gel column, using 1:1 benzene-ethyl acetate as an eluate, provides the purified product.

Workup

  1. additionthe addition
  2. customThe mixture is decanted into a cold saturated aqueous sodium bicarbonate solution
  3. extractionthe crude product is extracted (3 × 50 ml.) with methylene chloride
  4. dry with materialThe combined organic extracts are dried over magnesium sulfate
  5. concentrationconcentrated to an oil, which on chromatographing on a silica gel column
  6. customprovides the purified product

Sources & evidence

ORD record
ord-e2763e01ae254d67a9f3189a84c61727
Source dataset
uspto-grants-1976_07
Patent number
US03968231

Reaction notes

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