Chloroform → HCID 131710452, compound

HRID 1576486Notes

Reaction equation

HRID 1576486 reaction equation
[OH:1][C:2]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH2:4][CH2:3]1.[C:25](Cl)(=[O:28])[CH2:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl>O>[C:19]1([C:2]2([O:1][C:25](=[O:28])[CH2:26][CH3:27])[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][CH:11]=3)[CH2:6][CH2:7]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 62324Propionyl chloride2×HCID 12589402HCID 12589402, compound

Product 1

HCID 131710452HCID 131710452, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4 g. (0.0125 mole) of 3-[2-(4-hydroxy-4-phenylpiperidinyl)ethyl]indole, 1.19 g. (0.0125 mole) of propionyl chloride and 7 g. of potassium carbonate in 50 ml. of chloroform was allowed to stir for 2 hours. Then 0.4 g. of additional propionyl chloride was added and allowed to stir another 30 minutes. The mixture was treated with 50 ml. of water and allowed to stir 30 minutes. The chloroform layer was separated, dried over magnesium sulfate and evaporated under reduced pressure to an oil. The oil was crystallized from benzene-isooctane and yielded 3.0 g. (64%) of product which melted at 140°-142° C. After an additional recrystallization the analytical sample melted at 142°-144° C.

Workup

  1. additionA mixture of 4 g
  2. stirringto stir another 30 minutes
  3. additionThe mixture was treated with 50 ml
  4. stirringto stir 30 minutes
  5. customThe chloroform layer was separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure to an oil
  8. customThe oil was crystallized from benzene-isooctane
  9. customyielded 3.0 g
  10. customAfter an additional recrystallization the analytical sample melted at 142°-144° C.

Sources & evidence

ORD record
ord-0a71f9ab643d4d6ca32f80bd7e77846d
Source dataset
uspto-grants-1976_09
Patent number
USRE028973

Reaction notes

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