1-Methyl-3-phenylpropylamine → 1-[4-Methoxy-3-[2-(tetrahydro-2-pyranyloxy)ethoxy]phenyl]-2-(1-methyl-3-phenylpropyl)aminoethanol

HRID 1758719Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH:7]2[O:9][CH2:8]2)=[CH:5][C:4]=1[O:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1.[C:22]1([CH2:28][CH2:29][CH:30]([NH2:32])[CH3:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH:7]([OH:9])[CH2:8][NH:32][CH:30]([CH3:31])[CH2:29][CH2:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:5][C:4]=1[O:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1

Participants

Conditions

Temperature: 90 °C

Procedure

14.7 g of 4-methoxy-3-[2-(tetrahydro-2-pyranyloxy)ethoxy]styrene oxide was dissolved in 770 ml of ethanol, and 55 g of 4-phenyl-2-butylamine was added. The mixture was stirred at 90° C. for 40 minutes. After the reaction, the reaction mixture was concentrated under reduced pressure, and the residue was chromatographed on a silica gel column to afford 7.73 g (yield 34.9%) of 1-[4-methoxy-3-[2-(tetrahydro-2-pyranyloxy)ethoxy]phenyl]-2-(1-methyl-3-phenylpropyl)aminoethanol.

Workup

customAfter the reaction
concentrationthe reaction mixture was concentrated under reduced pressure
customthe residue was chromatographed on a silica gel column

Sources & evidence

ORD record: ord-9301e7f019534a529ecd02c383d418f8
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374840

Reaction notes

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