Potassium Carbonate → HCID 86735776, compound

HRID 839714Notes

Reaction equation

HRID 839714 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][CH:10]2[CH2:14][CH2:13][NH:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].O.O.[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34]>C1C=CC=CC=1>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[N:18]1([CH2:17][CH2:16][N:12]2[CH2:13][CH2:14][CH:10]([O:9][CH2:8][CH2:7][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH2:11]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 61373Oxalic acid dihydrateHCID 748271-(2-Chloroethyl)piperidineHCID 2133316470001-70-6

Product 1

HCID 86735776HCID 86735776, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 10.0 g. (0.051 mole) of 3-(2-piperidinoethoxy)pyrrolidine and 10.4 g. (0.07 mole) of 1-(2-chloroethyl)piperidine in 200 ml. dry benzene was stirred with 28 g. (0.2 mole) of potassium carbonate at reflux for 15 hr. After cooling, the reaction mixture was filtered and concentrated. The residual oil was molecularly distilled to give a slightly impure product which when treated with three equivalents of oxalic acid dihydrate gave 9.3 g. of the trioxalate salt, m.p. 155°-162° C. (32% yield). The salt was recrystallized from methanol to give 5.8 g. of white crystalline salt, m.p. 177°-179° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. distillationThe residual oil was molecularly distilled
  5. customto give a slightly impure product which when
  6. customgave 9.3 g
  7. customThe salt was recrystallized from methanol
  8. customto give 5.8 g

Sources & evidence

ORD record
ord-9b37900ae68a429da2e68e89059afa45
Source dataset
uspto-grants-1978_06
Patent number
US04096331

Reaction notes

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