Water → Hydrochloric Acid

HRID 1249182Notes

Reaction equation

HRID 1249182 reaction equation
[C:1]([N:4]([CH:13]([C:15]1([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[CH2:18][CH2:17][CH2:16]1)[CH3:14])[CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)(=[O:3])[CH3:2].O.[OH-].[Na+]>O1CCCC1.CCOCC>[ClH:25].[OH2:3].[ClH:25].[ClH:25].[CH2:1]([N:4]([CH:13]([C:15]1([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[CH2:16][CH2:17][CH2:18]1)[CH3:14])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1)[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13279957HCID 13279957, compound

Product 2

HCID 313Hydrochloric AcidHCID 20225052HCID 20225052, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Borane-methyl sulphide complex (4 ml) was added under a nitrogen atmosphere to a solution of the amide prepared as above (0.63 g) in dry tetrahydrofuran (50 ml). The mixture was stirred for 16 hours. The residue as cooled to 0° C. and water (30 ml) added and then 2.5N sodium hydroxide solution (30 ml) added. The basic mixture was extracted with ether and the extract was washed, dried filtered and evaporated to give an oil which was dissolved in ether and the solution filtered. Passing hydrogen chloride gas through the solution gave N-ethyl-N-(2-morpholino-ethyl)-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine dihydrochloride hydrate (m.p. 105°-115° C.).

Workup

  1. extractionThe basic mixture was extracted with ether
  2. washthe extract was washed
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oil which
  7. filtrationthe solution filtered

Sources & evidence

ORD record
ord-b9ea391020bc4b5f898b1af884412eb6
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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