Water → HCID 21481267, compound

HRID 435762Notes

Reaction equation

HRID 435762 reaction equation
Cl.[Cl:2][C:3]1[C:4]2[C:5]3[CH2:21][N:20]([CH2:22][CH2:23][CH2:24][CH:25]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[OH:26])[CH2:19][C:6]=3[N:7]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:8]=2[CH:9]=[CH:10][CH:11]=1.[OH2:34]>>[C:25]([OH:34])(=[O:26])[CH3:27].[Cl:2][C:3]1[C:4]2[C:5]3[CH2:21][N:20]([CH2:22][CH2:23][CH2:24][CH:25]([C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)[OH:26])[CH2:19][C:6]=3[N:7]([C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 962Water2×HCID 21481255HCID 21481255, compound

Product 1

HCID 21481267HCID 21481267, compound

Procedure

Five grams of 8-chloro-4-(p-fluorophenyl)-2-[4-(p-fluorophenyl)-4-hydroxybutyl]-1,2,3,4-tetrahydropyrrolo[3,4-b]indole hydrochloride in 75 ml. of water is treated with 3 ml. of water containing 1.0 g. of sodium hydroxide, and the liberated free base extracted into 150 ml. of diethyl ether. The ether layer is separated, dried over magnesium sulfate and treated with 1 ml. of glacial acetic acid. The organic solvent and excess acetic acid are removed under reduced pressure and the residue triturated with hexane and filtered.

Workup

  1. extractionof sodium hydroxide, and the liberated free base extracted into 150 ml
  2. customThe ether layer is separated
  3. dry with materialdried over magnesium sulfate
  4. additiontreated with 1 ml
  5. customThe organic solvent and excess acetic acid are removed under reduced pressure
  6. customthe residue triturated with hexane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-21672d9594a049be95bc111516b1d734
Source dataset
uspto-grants-1977_02
Patent number
US04006164

Reaction notes

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