Hydrochloric Acid → HCID 12821969, compound

HRID 2059097Notes

Reaction equation

HRID 2059097 reaction equation
[CH3:1][NH:2][CH3:3].Cl.[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]23[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[CH2:19][CH2:18][N:17]2[CH2:16][CH2:15][C:14](=O)[CH2:13]3)=[CH:8][CH:7]=1.[BH3-]C#N.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO.CCOCC>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]23[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[CH2:19][CH2:18][N:17]2[CH2:16][CH2:15][CH:14]([N:2]([CH3:3])[CH3:1])[CH2:13]3)=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 674Dimethylamine2×HCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydride2×HCID 12821968HCID 12821968, compound

Product 1

HCID 12821969HCID 12821969, compoundYield 24.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

To an ice-cold solution of 56 ml (2.16 M, 121 mmoles) of dimethyl amine in methanol is added 8 ml (5.0 N, 40 mmoles) of HCl in methanol. After 5 minutes, 5.9 g (20 mmoles) of 11b-(4-fluorophenyl)-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-one is added. Thereafter, 14 mmoles of NaBH3CN is added. After 24 hours, some molecular sieves are added. 24 hours later, additional molecular sieves are added. After a further 24 hours, an additional 14 mmoles of NaBH3CN is added. After still another 24 hours, 7.5 ml (2.16 M, 16.2 mmoles) of dimethylamine in methanol and 2.0 ml (5.0 N, 10 mmoles) of HCl are added. Three days later, the product is worked-up by pouring it into aqueous sodium carbonate and ether. The mixture is filtered through filter aid; the ether layer is washed with aqueous NaOH, brine and dried (MgSO4). After concentration in vacuo, 6.25 g (96%) of a semi-oily white crystalline solid, i.e., 11b-(4-fluorophenyl)-1,3,4,6,7,11b-hexahydro-N,N-dimethyl-2H-benzo[a]quinolizin-2-amine, is obtained. This product is recrystallized from 100 ml of cyclohexane, yielding 1.6 g of 11b-(4-fluorophenyl)-1,3,4,6,7,11b-hexahydro-N,N-dimethyl-2H-benzo[a]quinolizin-2-amine, m.p. 159°-167° C.

Workup

  1. waitAfter 24 hours
  2. additionsome molecular sieves are added
  3. addition24 hours later, additional molecular sieves are added
  4. waitAfter a further 24 hours
  5. waitAfter still another 24 hours
  6. customThree days
  7. filtrationThe mixture is filtered
  8. filtrationthrough filter aid
  9. washthe ether layer is washed with aqueous NaOH, brine
  10. dry with materialdried (MgSO4)
  11. concentrationAfter concentration in vacuo, 6.25 g (96%) of a semi-oily white crystalline solid, i.e., 11b-(4-fluorophenyl)-1,3,4,6,7,11b-hexahydro-N,N-dimethyl-2H-benzo[a]quinolizin-2-amine
  12. customis obtained
  13. customThis product is recrystallized from 100 ml of cyclohexane

Sources & evidence

ORD record
ord-bcfe8d61249c423f8d5dd43fab01448f
Source dataset
uspto-grants-1982_03
Patent number
US04321382

Reaction notes

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