Hydrochloric Acid → HCID 70608403, compound

HRID 426762Notes

Reaction equation

HRID 426762 reaction equation
C([N:8]1[CH2:16][CH:15]2[C:10](=[C:11]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:12]3[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:13]=3[CH2:14]2)[CH2:9]1)C1C=CC=CC=1.[BH4-].[Na+].Cl>O.C(O)C.Cl[Pd]Cl>[CH3:21][C:19]1[CH:18]=[CH:17][C:13]2[CH2:14][CH:15]3[CH:10]([CH:11]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:12]=2[CH:20]=1)[CH2:9][NH:8][CH2:16]3

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 70609185HCID 70609185, compound

Product 1

HCID 70608403HCID 70608403, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 0.55 g of palladium-II-chloride and 0.39 g of common salt in 50 cc of water is added at 25° to a solution of 35.2 g of (9aRS)-2-benzyl-9,9a-dihydro-6-methyl-4-phenyl-benz[f]isoindoline in 300 cc of ethanol. A solution of 2.0 g of sodium borohydride in 25 cc of water is added dropwise to the mixture at 0°, stirring is effected at 25° for 30 minutes, the pH of the solution is adjusted to 2 with aqueous concentrated hydrochloric acid, and hydrogenation is finally effected at 60° and a pressure of 4 atmospheres for 18 hours. The reaction mixture is filtered, the filtrate is concentrated, the residue is extracted with hot ethanol, and the clear solution is allowed to cool, whereby the hydrochloride salt form of the title compound, having a M.P. of 215°-220° (from methanol/ether), crystallizes.

Workup

  1. customis finally effected at 60°
  2. waita pressure of 4 atmospheres for 18 hours
  3. filtrationThe reaction mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. extractionthe residue is extracted with hot ethanol
  6. temperatureto cool
  7. customcrystallizes

Sources & evidence

ORD record
ord-e00f0e98cc954fb58288be676204dfe5
Source dataset
uspto-grants-1979_10
Patent number
US04171369

Reaction notes

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