Triethylamine → HCID 21535701, compound

HRID 1077046Notes

Reaction equation

HRID 1077046 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[CH2:7]1[O:16][C:10]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[O:9][CH2:8]1.C(N(CC)CC)C>ClCCl>[O:9]1[C:10]2([CH2:15][CH2:14][N:13]([C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])[CH2:12][CH2:11]2)[O:16][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 21535701HCID 21535701, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.4 g. of cyclopropanecarbonyl chloride in 150 ml. of dichloromethane is rapidly added to a solution of 12.5 g. of 4-piperidone ethylene acetal (1,4-dioxa-8-azaspiro[4.5]decane) and 20 g. of triethylamine in 200 ml. of dichloromethane, causing the solution to reflux. Heating to reflux with stirring is continued overnight; the mixture is cooled and the precipitated triethylammonium chloride filtered off. The mother liquor is concentrated to about half volume, washed with water, dried over anhydrous potassium carbonate, and stripped to dryness. The residual oil quickly solidifies, and on crystallization from 300 ml. hexane yields cyclopropyl 1,4-dioxa-8-azaspiro[4.5]dec-8-yl ketone, m.p. 72°-74°, as white needles. Reduction of 14.0 g. of this compound in 60 ml. freshly chromatographed, peroxide-free ether by dropwise addition to a suspension of 2.5 g. of lithium aluminum hydride in similarly treated ether, followed by three hours of refluxing, yields 8-(cyclopropylmethyl)-1,4-dioxa-8azaspiro[4.5]decane as a colorless oil. Hydrolysis of this ethylene acetal by refluxing in 2N hydrochloric acid, followed by basification with 50% sodium hydroxide, extraction into ether, drying of the extrct, and stripping off the solvent, yields a crude product which distills at 111°-122°/16 mm. to give 1-(cyclopropylmethyl)-4-piperidone, shown by gas-liquid chromatography to be 95-99% pure.

Workup

  1. temperatureto reflux
  2. temperatureHeating
  3. temperatureto reflux
  4. temperaturethe mixture is cooled
  5. filtrationthe precipitated triethylammonium chloride filtered off
  6. concentrationThe mother liquor is concentrated to about half volume
  7. washwashed with water
  8. dry with materialdried over anhydrous potassium carbonate
  9. customon crystallization from 300 ml

Sources & evidence

ORD record
ord-c46a5d30524440488fac17c42dc2cffc
Source dataset
uspto-grants-1976_05
Patent number
US03959300

Reaction notes

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