Hydrochloric Acid → HCID 13423963, compound

HRID 1980250Notes

Reaction equation

HRID 1980250 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([O:24][CH2:25][CH3:26])([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][CH3:23])[CH2:9]1)C1C=CC=CC=1.[ClH:27]>[Pd].C(O)C>[ClH:27].[CH2:25]([O:24][C:10]1([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][CH3:23])[CH2:11][CH2:12][NH:8][CH2:9]1)[CH3:26]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13423964HCID 13423964, compound

Product 1

HCID 13423963HCID 13423963, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 10.4 g (0.029 mole) of 1-benzyl-3-ethoxy-3-[(2-ethoxyphenoxy)methyl]pyrrolidine in 100 ml of 200 ethanol was treated with palladium/carbon catalyst and shaken at 70° C. under a hydrogen atmosphere for 16 hours. No hydrogen was absorbed. The catalyst was removed by filtration, the filter cake washed with 50 ml of 200 ethanol, the filtrate transferred to a Parr reaction bottle and treated with 29 ml of 1.00N hydrochloric acid. Palladium/carbon catalyst was added and the reaction mixture was shaken under a hydrogen atmosphere at 70° C. for 16 hours. The catalyst was removed by filtration, and the filtrate evaporated under reduced pressure (9.0 g). The product hydrochloride crystallized on standing and was recrystallized twice from isopropanol-isopropyl ether: 5.7 g, (65%), m.p., 109°-112° C. The salt was dried under vacuum.

Workup

  1. customNo hydrogen was absorbed
  2. customThe catalyst was removed by filtration
  3. washthe filter cake washed with 50 ml of 200 ethanol
  4. customthe filtrate transferred to a Parr reaction bottle
  5. stirringthe reaction mixture was shaken under a hydrogen atmosphere at 70° C. for 16 hours
  6. customThe catalyst was removed by filtration
  7. customthe filtrate evaporated under reduced pressure (9.0 g)
  8. customThe product hydrochloride crystallized
  9. customwas recrystallized twice from isopropanol-isopropyl ether
  10. customm.p., 109°-112° C
  11. customThe salt was dried under vacuum

Sources & evidence

ORD record
ord-7587e47ecb4f4b169f29bcf056629178
Source dataset
uspto-grants-1985_04
Patent number
US04508724

Reaction notes

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