Pyridine → HCID 86736138, compound

HRID 1703574Notes

Reaction equation

HRID 1703574 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([OH:23])[CH2:22][CH2:21][CH2:20][CH:19]3[CH:15]2[CH2:16][CH2:17][NH:18]3)=[CH:10][CH:9]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2([OH:23])[CH2:22][CH2:21][CH2:20][CH:19]3[CH:15]2[CH2:16][CH2:17][N:18]3[C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:5])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 86736139HCID 86736139, compound

Product 1

HCID 86736138HCID 86736138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The starting material was produced as follows: 2.74 g of Cyclopropanecarboxylic acid chloride was added dropwise to a solution of 7.2 g of (3aRS, 4SR, 7aRS)-4-p-chlorophenylhexahydro-4-indolinol and 2.5 ml of pyridine in 30 ml of methylene chloride at 0° to 10°. The mixture was stirred at room temperature for 1 hour, and then was washed first with a 10% tartaric acid solution, then with a sodium bicarbonate solution, then with a saturated salt solution. The organic phase was dried over sodium sulphate and concentrated to afford (3aRS, 4SR, 7aRS)-4-p-chlorophenyl-1-cyclopropylcarbonylhexahydro-4-indolinol. (M.P. 167°-169°).

Workup

  1. customThe starting material was produced
  2. washwas washed first with a 10% tartaric acid solution
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8f5ca77e22f34f04a13dc81c3bd4bcf7
Source dataset
uspto-grants-1978_11
Patent number
US04124719

Reaction notes

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