Hydrochloric Acid → HCID 70457521, compound

HRID 1249204Notes

Reaction equation

HRID 1249204 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:25][CH3:26])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:15])=[CH:9][CH:8]=1)(OC)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[ClH:35]>O1CCCC1.O>[OH2:2].[ClH:35].[OH:2][CH2:1][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH:14]([NH:16][CH2:17][CH:18]([O:25][CH3:26])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:15])=[CH:11][CH:12]=1.[OH:2][CH2:1][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH:14]([NH:16][CH2:17][CH:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:25][CH3:26])[CH3:15])=[CH:11][CH:12]=1.[ClH:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20225230HCID 20225230, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 70457521HCID 70457521, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-methoxy-2-phenylethanamine (3.09 g) in dry tetrahydrofuran (30 ml) was added dropwise, with stirring, to a suspension of lithium aluminium hydride (1.65 g) in dry tetrahydrofuran (40 ml) and the resultant mixture heated under reflux for five hours. After cooling, water (1.7 ml), 10% aqueous sodium hydroxide (1.7 ml) and water (3.4 ml) were added carefully. Filtration and evaporation of the filtrate to dryness gave an oil which was converted to its hydrochloride salt by addition of ethereal hydrogen chloride. Crystallisation from methanol-ethyl acetate gave the title compound, mp 100°-2° C., as a 90:10 mixture of diastereoisomers.

Workup

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

Sources & evidence

ORD record
ord-4de354315513481a8cf9bcb9d82d2b3c
Source dataset
uspto-grants-1986_12
Patent number
US04629737

Reaction notes

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