Chloroform → HCID 54016229, compound

HRID 1576481Notes

Reaction equation

HRID 1576481 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH2:3]1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[C:23](Cl)=[O:24].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)(Cl)Cl>O>[CH3:32][O:31][C:27]1[CH:26]=[C:22]([CH:21]=[C:20]([O:19][CH3:18])[C:28]=1[O:29][CH3:30])[C:23]([O:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH2:3]1)=[O:24]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 21510684HCID 21510684, compound

Product 1

HCID 54016229HCID 54016229, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3 g. (0.013 mole) of 3-[2-(3-hydroxypyrrolidinyl)ethyl]indole, 3 g. (0.013 mole) of 3,4,5-trimethoxybenzoyl chloride and 5 g. (0.05 mole) of sodium carbonate in 40 ml. of chloroform was stirred under anhydrous conditions for 24 hours. Then 0.3 g. of additional acid chloride was added and the mixture stirred another 24 hours. The mixture was treated with 50 ml. of water, stirred for 1 hour and the chloroform layer separated and dried over magnesium sulfate. Evaporation of the chloroform on a rotating evaporator gave an oil which would not crystallize.

Workup

  1. additionA mixture of 3 g
  2. additionThe mixture was treated with 50 ml
  3. customthe chloroform layer separated
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the chloroform
  6. customon a rotating evaporator
  7. customgave an oil which would not
  8. customcrystallize

Sources & evidence

ORD record
ord-65e8446385424b77bdd7e7a04d1d4de4
Source dataset
uspto-grants-1976_09
Patent number
USRE028973

Reaction notes

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