Triethylamine → HCID 20403159, compound

HRID 2198474Notes

Reaction equation

HRID 2198474 reaction equation
[CH2:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH:8]=[CH:7]2)[CH2:5][CH2:4][CH2:3][NH:2]1.Br[CH2:13][CH2:14][OH:15].C(N(CC)CC)C>C1(C)C=CC=CC=1>[OH:15][CH2:14][CH2:13][CH:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH:8]=[CH:7]2)[CH2:5][CH2:4][CH2:3][NH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 20403147HCID 20403147, compound

Product 1

HCID 20403159HCID 20403159, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-azaspiro-[5.5]-undec-7-ene (30.2 g.; 0.20 mole), 2-bromoethanol (25 g.; 0.20 mole) and triethylamine (20.2 g.) in toluene (250 ml.) is heated under reflux for 5 hours. The solution is cooled, filtered to remove triethylamine hydrobromide and the filtrate concentrated under reduced pressure. The residual liquid is distilled under reduced pressure to afford 28 g. (72% yield) of 2-hydroxyethyl-2-azaspiro-[5.5]-undec-7-ene, b.p. 90°-91° C./0.45 mm.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 5 hours
  3. temperatureThe solution is cooled
  4. filtrationfiltered
  5. customto remove triethylamine hydrobromide
  6. concentrationthe filtrate concentrated under reduced pressure
  7. distillationThe residual liquid is distilled under reduced pressure
  8. customto afford 28 g

Sources & evidence

ORD record
ord-7bd2a86e6f644581815fd0aee0f7710f
Source dataset
uspto-grants-1982_11
Patent number
US04357471

Reaction notes

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