Ethylene Glycol → HCID 68760355, compound

HRID 325923Notes

Reaction equation

HRID 325923 reaction equation
C([N:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[C@H:11]([CH3:24])[CH2:10]1)(=O)C1C=CC=CC=1.[OH-].[K+].C(O)CO>O>[CH3:24][C@H:11]1[C@@H:12]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:13][CH2:14][NH:9][CH2:10]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 70473586HCID 70473586, compound

Product 1

HCID 68760355HCID 68760355, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
130 °C

Procedure

A mixture of 21 parts of cis-1-benzoyl-4-(1H-indol-3-yl)-3-methylpiperidine, 60 parts of potassium hydroxide 385 parts of 1,2-ethanediol and 80 parts of water was stirred and refluxed (about 130° C.) overnight. After cooling for a while, about 200 parts of water were added whereupon the product was crystallized. The whole was further cooled and the solid product was filtered off, washed with a lot of water and with 2,2'-oxybispropane and dried, yielding 11.2 parts (80%) of cis-3-(3-methyl-4-piperidinyl)-1H-indole (intermediate 23).

Workup

  1. additionwere added whereupon the product
  2. customwas crystallized
  3. temperatureThe whole was further cooled
  4. filtrationthe solid product was filtered off
  5. washwashed with a lot of water and with 2,2'-oxybispropane
  6. customdried

Sources & evidence

ORD record
ord-723036dbb10947a187b1721e9e5bb219
Source dataset
uspto-grants-1984_04
Patent number
US04443451

Reaction notes

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