1,4-Dioxa-8-azaspiro(4.5)decane → HCID 22120330, compound

HRID 1274109Notes

Reaction equation

HRID 1274109 reaction equation
O1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[ClH:11].[F:12][C:13]1[CH:18]=CC(ON)=[CH:15][CH:14]=1>Cl>[ClH:11].[F:12][C:13]1[CH:18]=[CH:2][C:3]2[O:4][C:5]3[CH2:10][CH2:9][NH:8][CH2:7][C:6]=3[C:15]=2[CH:14]=1

Participants

4

Reactant 2

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 22120336O-(4-fluorophenyl)hydroxylamine hydrochloride

Product 1

HCID 22120330HCID 22120330, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1,4-dioxa-8-azaspiro[4,5]decane (0.12 mol) was added dropwise to a mixture of O-(4-fluorophenyl)hydroxylamine hydrochloride (1: 1) (0.1 mol) in a mixture of HCl and 1,1-oxybisethane (150 ml). The reaction mixture was stirred and refluxed for 4 hours and then cooled. The precipitate was filtered off and dried, then recrystallized from water, yielding 10 g (43.9%) 1,2,3,4-tetrahydro-8-fluorobenzofuro[3,2-c]pyridine hydrochloride (interm. 2; mp. >300° C.).

Workup

  1. temperaturerefluxed for 4 hours
  2. temperaturecooled
  3. filtrationThe precipitate was filtered off
  4. customdried
  5. customrecrystallized from water

Sources & evidence

ORD record
ord-d454cc75c4f441a4906331fb4785545f
Source dataset
uspto-grants-2000_12
Patent number
US06156757

Reaction notes

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