Benzaldehyde → N-benzyl-3-[4-(2-(cyclopropylmethoxy)ethyl)phenoxy]-2-hydroxypropylamine

HRID 1906674Notes

Reaction equation

HRID 1906674 reaction equation
[CH:1]1([CH2:4][O:5][CH2:6][CH2:7][C:8]2[CH:19]=[CH:18][C:11]([O:12][CH2:13][CH:14]([OH:17])[CH2:15][NH2:16])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C.[Pd]>[CH2:20]([NH:16][CH2:15][CH:14]([OH:17])[CH2:13][O:12][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[CH:19][CH:18]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 140252973-[4-(2-(Cyclopropylmethoxy)ethyl)phenoxy]-2-hydroxypropylamine

Product 1

HCID 14025301N-benzyl-3-[4-(2-(cyclopropylmethoxy)ethyl)phenoxy]-2-hydroxypropylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent3×

Procedure

In an alternative method, 3-[4-(2-(cyclopropylmethoxy)ethyl)phenoxy]-2-hydroxypropylamine (1.33 g), (see Example 5 (i) in ethanol (20 ml) was stirred at room temperature whilst a solution of benzaldehyde (1.06 g) in ethanol (20 ml) was added. The mixture was poured on to a slurry of 5% palladium on charcoal (0.5 g) in ethanol (5 ml) and hydrogenated at 344 kPa (50 p.s.i.) for 10 minutes. The mixture was filtered through diatomaceous earth and the filtrate evaporated to give a clear oil which crystallised on standing to give N-benzyl-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-2-hydroxypropylamine, in quantitative yield, identical to an authentic sample by chromatography and a nuclear magnetic resonance spectrum.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. customthe filtrate evaporated
  4. customto give a clear oil which
  5. customcrystallised

Sources & evidence

ORD record
ord-331ce044c7484f19bf239d276f177f8a
Source dataset
uspto-grants-1987_03
Patent number
US04652563

Reaction notes

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