Hydrochloric Acid → HCID 9808461, compound

HRID 2305262Notes

Reaction equation

HRID 2305262 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[ClH:15].Cl.[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[C:25](=[O:39])[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])[CH2:30][CH2:29]1.[NH4+].[Cl-].Cl>C1COCC1.C(OCC)C>[ClH:17].[ClH:15].[C:6]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:8][C:3]([C:25]([C:19]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=2[Cl:17])([OH:39])[CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][CH:31]([CH2:34][CH2:35][N:36]([CH3:37])[CH3:38])[CH2:30][CH2:29]2)=[CH:4][CH:5]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 71014-Bromobiphenyl2×HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 18432011HCID 18432011, compound

Product 1

HCID 9808461HCID 9808461, compoundYield 15.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The Grignard reaction was started with magnesium (0.08 mol) and a few ml of a mixture of 4-bromobiphenyl (0.08 mol) in THF (150 ml). Then the rest of the mixture of 4-bromobiphenyl in THF was added dropwise. The resulting reaction mixture was stirred and refluxed for 1 hour and then cooled. 1-(2,4-dichlorophenyl)-3-[4-[2-(dimethylamino)ethyl]-1-piperidinyl]-1-propanone dihydrochloride (0.023 mol) dissolved in diethyl ether (50 ml) was added dropwise. The mixture was stirred and refluxed for 1 hour, then cooled, decomposed with NH4Cl 10% and stirred. A diluted aqueous HCl solution was added. The mixture was stirred for a while. The organic layer was separated, washed with H2O, dried and filtered. The filtrate was saturated with HCl/2-propanol. The precipitate was filtered off and crystallized from CH3OH and diethyl ether. The precipitate was filtered off and dried, yielding 1.05 g (7.8%) of (±)-α-[(1,1 ′-biphenyl)-4-yl]-a-(2,4-dichlorophenyl)-4-[2-(dimethylamino)ethyl]-1-piperidine-propanol dihydrochloride (comp. 34).

Workup

  1. customThe Grignard reaction
  2. additionwas added dropwise
  3. customThe resulting reaction mixture
  4. temperaturerefluxed for 1 hour
  5. temperaturecooled
  6. additionwas added dropwise
  7. stirringThe mixture was stirred
  8. temperaturerefluxed for 1 hour
  9. temperaturecooled
  10. stirringstirred
  11. stirringThe mixture was stirred for a while
  12. customThe organic layer was separated
  13. washwashed with H2O
  14. customdried
  15. filtrationfiltered
  16. filtrationThe precipitate was filtered off
  17. customcrystallized from CH3OH and diethyl ether
  18. filtrationThe precipitate was filtered off
  19. customdried

Sources & evidence

ORD record
ord-29e601034d384f67bfa3b22759047f77
Source dataset
uspto-grants-2002_08
Patent number
US06440440B1

Reaction notes

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