HCID 12760485, compound → HCID 12760487, compound

HRID 1578153Notes

Reaction equation

HRID 1578153 reaction equation
[CH2:1]([N:17]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:18](=O)[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1C=CC=CC=1>[CH2:1]([N:17]([CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 12760485HCID 12760485, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 12760487HCID 12760487, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

N,N-Dihexadecyl-4-(aminomethyl)phenoxy acetamide (2.8 g, 0.0042 mole) was dissolved in benzene (30 ml) and treated with sodium bis-(2-methoxyethoxy)-aluminum hydride (5.94 g of a 70% solution in benzene). The mixture was refluxed for 16 hours, cooled and quenched with 10% sodium hydroxide solution (10.2 ml). The organic phase was separated, washed with saturated sodium chloride solution (3×50 ml), dried over sodium sulfate, filtered and concentrated under vacuum to an oil (2.27 g). The product was purified by silica gel chromatography (eluted with a chloroform/ethanol gradient mixture), converted to the hydrochloride salt, and recrystallized from ethanol/acetonitrile (1:1) to give the desired ethyl amine (0.725 g, 25% yield), mp 231°-238° C.

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. temperaturecooled
  3. customquenched with 10% sodium hydroxide solution (10.2 ml)
  4. customThe organic phase was separated
  5. washwashed with saturated sodium chloride solution (3×50 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum to an oil (2.27 g)
  9. customThe product was purified by silica gel chromatography (
  10. washeluted with a chloroform/ethanol gradient mixture),
  11. customrecrystallized from ethanol/acetonitrile (1:1)

Sources & evidence

ORD record
ord-88c2631aa53d4155a3c63ba565bbd7a4
Source dataset
uspto-grants-1981_09
Patent number
US04291060

Reaction notes

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