Hydrochloric Acid → 2,3,4,4a,6,7,11b,12,13,13a-decahydro-9,10-dimethoxy-13-phenyl-1H-dibenzo[a,f]quinolizin-13-ol hydrochloride

HRID 839507

Reaction equation

HRID 839507 reaction equation
[CH3:1][O:2][C:3]1[C:21]([O:22][CH3:23])=[CH:20][C:6]2[CH:7]3[N:12]([CH2:13][CH2:14][C:5]=2[CH:4]=1)[CH:11]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:10]1[C:9](=[O:19])[CH2:8]3.[C:24]1([Mg]Br)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Cl-:32].[NH4+].Cl>O1CCCC1.CCOCC>[ClH:32].[CH3:1][O:2][C:3]1[C:21]([O:22][CH3:23])=[CH:20][C:6]2[CH:7]3[N:12]([CH2:13][CH2:14][C:5]=2[CH:4]=1)[CH:11]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:10]1[C:9]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([OH:19])[CH2:8]3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 127744922,3,4,4a,6,7,11b,12,13,13a-decahydro-9,10-dimethoxy-1H-dibenzo[a,f]quinolizin-13-oneHCID 178418255HCID 178418255, compound

Product 1

HCID 203233152,3,4,4a,6,7,11b,12,13,13a-decahydro-9,10-dimethoxy-13-phenyl-1H-dibenzo[a,f]quinolizin-13-ol hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 6.3 g (0.02 mole) of 2,3,4,4a,6,7,11b,12,13,13a-decahydro-9,10-dimethoxy-1H-dibenzo[a,f]quinolizin-13-one in 100 ml of tetrahydrofuran is added dropwise 30 ml of a 2N solution of phenylmagnesium bromide in tetrahydrofuran. When the addition is complete, the mixture is refluxed for three hours and cooled after which 100 ml of saturated ammonium chloride solution is added. The organic and aqueous layers are separated and the aqueous layer is extracted with ether. The combined organic layers are dried over magnesium sulfate, filtered and evaporated in vacuo leaving an oily residue which is dissolved in dry ether and treated with excess ethereal hydrochloric acid. The resulting precipitate is collected and recrystallized from benzene-methanol to give 2,3,4,4a,6,7,11b,12,13,13a-decahydro-9,10-dimethoxy-13-phenyl-1H-dibenzo[a,f]quinolizin-13-ol hydrochloride, M.P. 227°-228° C.

Workup

  1. additionWhen the addition
  2. temperaturethe mixture is refluxed for three hours
  3. additionis added
  4. customThe organic and aqueous layers are separated
  5. extractionthe aqueous layer is extracted with ether
  6. dry with materialThe combined organic layers are dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customleaving an oily residue which
  10. customThe resulting precipitate is collected
  11. customrecrystallized from benzene-methanol

Sources & evidence

ORD record
ord-0a6e080b843249de94abc4c33106a7ad
Source dataset
uspto-grants-1978_06
Patent number
US04096147

Linked notes

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