Allylamine → HCID 86733941, compound

HRID 1576257Notes

Reaction equation

HRID 1576257 reaction equation
CS(O[CH2:6][CH2:7][C:8]1([CH2:24][CH2:25]OS(C)(=O)=O)[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([O:22][CH3:23])[C:16]=2[CH2:15][C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)(=O)=O.[CH2:31]([NH2:34])[CH:32]=[CH2:33]>C(O)CC>[CH2:31]([N:34]1[CH2:25][CH2:24][C:8]2([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([O:22][CH3:23])[C:16]=3[CH2:15][C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:7][CH2:6]1)[CH:32]=[CH2:33]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 21514910HCID 21514910, compound

Product 1

HCID 86733941HCID 86733941, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 9,9-di(2-methanesulphonyloxyethyl)-4-methoxy-9,10-dihydroanthracene (1.5 g.) and allylamine (7.0 g.) in n-propanol (30 ml.) is heated under reflux for 18 hours. The solvent is evaporated and 2N sodium hydroxide (20 ml.) is added; the suspension is extracted with ether and the ether layer washed with water, and extracted with 2N hydrochloric acid. The acid extract is washed with ether, basified with 15N ammonia solution, and the precipitated product is extracted into ether, the ether is washed with water and with brine, dried (MgSO4) and evaporated to give 1'-allyl-4-methoxy-9,10-dihydroanthracene-9-spiro-4'-piperidine as an oil.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvent is evaporated
  4. addition2N sodium hydroxide (20 ml.) is added
  5. extractionthe suspension is extracted with ether
  6. washthe ether layer washed with water
  7. extractionextracted with 2N hydrochloric acid
  8. extractionThe acid extract
  9. washis washed with ether
  10. extractionthe precipitated product is extracted into ether
  11. washthe ether is washed with water and with brine
  12. dry with materialdried (MgSO4)
  13. customevaporated

Sources & evidence

ORD record
ord-5aff4122b4574dd9b8ac472149a40636
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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