Triethylamine → HCID 20403159, compound

HRID 435165Notes

Reaction equation

HRID 435165 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 removed triethylamine hydrobromide and the filtrate concentrated under reduced pressure. The residue 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 removed triethylamine hydrobromide
  6. concentrationthe filtrate concentrated under reduced pressure
  7. distillationThe residue liquid is distilled under reduced pressure
  8. customto afford 28 g

Sources & evidence

ORD record
ord-058aed6fd5bd461088789669197a4c43
Source dataset
uspto-grants-1983_08
Patent number
US04400512

Reaction notes

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