Benzyl Chloride → HCID 12900681, compound

HRID 1155679Notes

Reaction equation

HRID 1155679 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[OH-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 913454-Chloroindole

Product 1

HCID 12900681HCID 12900681, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 16.9 g of 4-chloro-1H-indole, 170 ml of benzene, 85 ml of aqueous 50% sodium hydroxide solution, 1.89 g of n-tetrabutyl ammonium hydrogen sulfate and 16.6 ml of benzyl chloride was heated at 60° C. with strong stirring for 4 hours and was then cooled to room temperature. The decanted organic phase was washed with water, dried and evaporated to dryness. The 30.2 g of residue were chromatographed over silica gel and were eluted with cyclohexane to obtain 22.8 g of 4-chloro-1-benzyl-1H-indole melting at 58°-60° C.

Workup

  1. temperaturewas then cooled to room temperature
  2. washThe decanted organic phase was washed with water
  3. customdried
  4. customevaporated to dryness
  5. customThe 30.2 g of residue were chromatographed over silica gel
  6. washwere eluted with cyclohexane

Sources & evidence

ORD record
ord-592929fe0dbc46b284062d6f52c22acc
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Reaction notes

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