Hydrochloric Acid → HCID 20186773, compound

HRID 2309009Notes

Reaction equation

HRID 2309009 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:16][CH2:17][CH:18]([O:26][CH2:27][CH2:28][OH:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH3:15])=[CH:9][CH:8]=1)(OC)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].Cl>O1CCCC1.O>[ClH:25].[OH:2][CH2:1][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:16][CH2:17][CH:18]([O:26][CH2:27][CH2:28][OH:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH3:15])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21285459HCID 21285459, compound

Product 1

HCID 20186773HCID 20186773, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-(2-hydroxyethoxy)-2-(3-chlorophenyl)ethanamine (3.0 g) in dry tetrahydrofuran (30 ml) was added dropwise, with stirring, to a suspension of lithium aluminium hydride (1.0 g) in dry tetrahydrofuran (30 ml) and the resultant mixture heated under reflux for 3 hours. After cooling, water (1 ml), 10% aqueous sodium hydroxide (1 ml) and water (2 ml) were added carefully. Filtration and evaporation of the filtrate to dryness gave an oil which was converted to its hydrochloride salt by treatment with ethereal hydrogen chloride. Recrystallisation from ethyl acetate-methanoldiethyl ether gave the title compound, mp 86°-90° C. as a 49:51 mixture of diastereoisomers.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. filtrationFiltration and evaporation of the filtrate to dryness
  4. customgave an oil which
  5. customRecrystallisation from ethyl acetate-methanoldiethyl ether

Sources & evidence

ORD record
ord-1b32116c5d634e5dba2f33a89033212f
Source dataset
uspto-grants-1987_09
Patent number
US04692465

Reaction notes

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