Hydrochloric Acid → HCID 20431221, compound

HRID 2412850

Reaction equation

HRID 2412850 reaction equation
[ClH:1].[CH3:2][CH:3]1[O:8][CH:7]([CH3:9])[CH2:6][NH:5][CH2:4]1.[C:10]([C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:23])[CH2:21][CH3:22])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].[CH2:24]=O.Cl>C(O)C>[ClH:1].[C:10]([C:14]1[CH:15]=[CH:16][C:17]([C:20](=[O:23])[CH:21]([CH3:24])[CH2:22][N:5]2[CH2:6][CH:7]([CH3:9])[O:8][CH:3]([CH3:2])[CH2:4]2)=[CH:18][CH:19]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5952814'-(tert-Butyl)propiophenoneHCID 193747542,6-Dimethylmorpholine hydrochloride

Product 1

HCID 20431221HCID 20431221, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

57.6 g (0.5 mole) of 2,6-dimethylmorpholine hydrochloride, 95.2 g (0.5 mole) of p-tert.-butyl-propiophenone and 25 g (0.83 mole) of paraformaldehyde were heated under reflux in 200 ml of ethanol for 1 hour. After adding 0.7 ml of concentrated hydrochloric acid, the reaction mixture was stirred under reflux for a further 15 hours. It was then concentrated, the residue was taken up in chloroform and the chloroform mixture was washed twice with water, dried over sodium sulphate and concentrated. The solid residue was suspended in hot ethyl acetate, filtered off and dried. 47.6 g (30% of theory) of p-tert.-butyl-2-methyl-3-(2,6-dimethylmorpholin-4yl)-propionphenone hydrochloride were obtained and were dissolved in aqueous sodium bicarbonate solution and the solution and 25 g (0.83 mole) of paraformaldehyde were heated under reflux in 200 ml of ethanol for 1 hour. After adding 0.7 ml of concentrated hydrochloric acid, the reaction mixture was stirred under reflux for a further 15 hours. It was then concentrated, the residue was taken up in chloroform and the chloroform mixture was washed twice with water, dried over sodium sulphate and concentrated. The solid residue was suspended in hot ethyl acetate, filtered off and dried. 47.6 g (30% of theory) of p-tert.-butyl-2-methyl-3-(2,6-dimethylmorpholin-4yl)-propionphenone hydrochloride were obtained and were dissolved in aqueous sodium bicarbonate solution and the solution was then extracted with ethyl acetate and the product phase concentrated. A quantative yield of the free base of boiling point 145°-48° C./0.12 mm Hg column was obtained. ##STR59##

Workup

  1. temperatureunder reflux for a further 15 hours
  2. concentrationIt was then concentrated
  3. washthe chloroform mixture was washed twice with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-c551a54059394019a83b0b00aa5a94ca
Source dataset
uspto-grants-1985_01
Patent number
US04495184

Linked notes

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