Hydrochloric Acid → HCID 11779419, compound

HRID 975840Notes

Reaction equation

HRID 975840 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]3([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[NH:13][CH2:12][CH2:11][CH:10]=2)=[CH:5][CH:4]=1>CCOCC.ClCCl>[ClH:2].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]3([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[NH:13][CH2:12][CH2:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10220867HCID 10220867, compound2×

Product 1

HCID 11779419HCID 11779419, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

5M Hydrochloric acid (200 ml) was added slowly to a solution of 5-(4-chlorophenyl)-1-azaspiro[5.5]undec-4-ene (98 g) in ether (1 l) and the mixture was stirred at ambient temperature for 30 minutes. The resulting solid was collected by filtration and washed with cold water followed by dichloromethane to give an off-white solid. The process was repeated using the remainder of 5-(4-chlorophenyl)-1-azaspiro[5.5]undec-4-ene to give further off-white solid. The combined solids were stirred in dichloromethane (1 l) for 1 hour, collected by filtration, washed with dichloromethane (200 ml) and dried in vacuo to give 5-(4-chlorophenyl)-1-azaspiro[5.5]undec-4-ene hydrochloride as an off-white solid. Yield 224.3 g, mp >300° C.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with cold water
  3. customto give an off-white solid
  4. customto give further off-white solid
  5. filtrationcollected by filtration
  6. washwashed with dichloromethane (200 ml)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a9047464546946a8a72f91be8ae4c986
Source dataset
uspto-grants-1997_03
Patent number
US05610161

Reaction notes

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