Phenylacetaldehyde → HCID 20839307, compound

HRID 1681366Notes

Reaction equation

HRID 1681366 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[O:10][CH2:11][CH2:12][NH2:13])=[CH:5][CH:4]=1.[C:21]1([CH2:27][CH:28]=O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH3-]C#N.[Na+].O1CCCC1.[C:39]([O-:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([O-:44])=[O:43].C(O)(=O)/C=C\C(O)=O>CCOCC.CO>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)[O:10][CH2:11][CH2:12][NH:13][CH2:28][CH2:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:7][CH:8]=1

Participants

9

Reactant 6

HCID 998PhenylacetaldehydeHCID 8028TetrahydrofuranHCID 444266Maleic AcidHCID 5003444Sodium cyanoborohydrideHCID 5288227Maleate(2-)HCID 700913072-[Bis(4-fluorophenyl)methoxy]ethan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 20839307HCID 20839307, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

0.017 Mol of this phthalimido derivative was dissolved in ethanol and hydrazine hydrochloride (0.088 mol) was added. The mixture was heated at 100° C. for three hrs., then the reaction mixture was cooled, the phthalhydrazide formed during the reaction was removed by filtration and the filtrate was concentrated. The amino derivative obtained was purified by transforming it in ether into the hydrochloride to yield 70% of 2-[bis(4-fluorophenyl)methoxy]ethanamine hydrochloride. Equimolar amounts of 2-[bis(4-fluorophenyl)methoxy]-ethanamine hydrochloride, benzeneethanal and NaBH3CN were dissolved in dry tetrahydrofuran (50 ml for 0.01 mol) and a few ml of methanol were also added. The mixture was left at room temperature with stirring overnight. The solid material was filtered off, the filtrate was evaporated and the residue was dissolved in dichloromethane. This solution was dried with sodium sulfate, filtered and concentrated. The compound was purified by flash column chromatography by using a mixture of petroleum ether/ethyl acetate in a ratio 7:3 increasing to 6:4. The eluent was previously saturated with ammonia gas. The free base obtained was transformed into the (Z)-2-butenedioate by adding maleic acid in ether, which was crystallized from a mixture of ether and methanol (10:1) to give N-[2-(bis(4-fluorophenyl)-methoxy)ethyl]benzeneethanamine (Z)-2-butenedioate (1:1) salt. m.p. 145°-147° C.

Workup

  1. waitThe mixture was left at room temperature
  2. filtrationThe solid material was filtered off
  3. customthe filtrate was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. dry with materialThis solution was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe compound was purified by flash column chromatography
  9. additiona mixture of petroleum ether/ethyl acetate in a ratio 7:3 increasing to 6:4
  10. customThe free base obtained
  11. customwas crystallized from a mixture of ether and methanol (10:1)

Sources & evidence

ORD record
ord-f2dfb82c183842c7a2901fa8e7811d8f
Source dataset
uspto-grants-1992_12
Patent number
US05171752

Reaction notes

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