Methylparaben → N,N-Diisopropyl-3-[(5-methoxycarbonyl)-2-hydroxy)phenyl]-3-phenyl-propylamine

HRID 41660Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH:12]([N:15]([CH:26]([CH3:28])[CH3:27])[CH2:16][CH2:17][CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)O)([CH3:14])[CH3:13]>CS(O)(=O)=O>[CH:26]([N:15]([CH:12]([CH3:14])[CH3:13])[CH2:16][CH2:17][CH:18]([C:11]1[CH:10]=[C:5]([CH:4]=[CH:3][C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 52.5 °C

Procedure

Methyl 4-hydroxy-benzoate (52.0 g, 340 mmol) is suspended in methanesulfonic acid (90 ml) in a round-bottom flask under inert atmosphere and the mixture is heated at a temperature of 50-55° C. 3-Diisopropylamino-1-phenyl-propan-1-ol (20.0 g, 85.0 mmol) is slowly added in about 2 hours and the mixture is reacted while hot for 5-6 hours. The mixture is cooled at room temperature and slowly poured in ice/water (200 g) under strong stirring. The product is extracted with dichloromethane (200 ml) and the organic phase is washed with a 10% sodium hydroxide solution (2×100 ml), then with an ammonium chloride aqueous solution until neutral pH. 28.9 g of a product are obtained in 92% yield.

Workup

customthe mixture is reacted while hot for 5-6 hours
temperatureThe mixture is cooled at room temperature
extractionThe product is extracted with dichloromethane (200 ml)
washthe organic phase is washed with a 10% sodium hydroxide solution (2×100 ml)

Sources & evidence

ORD record: ord-69e317fd0d0c49f4b00d938a29029421
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530691B2

Reaction notes

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