Phenethylamine → HCID 49801658, compound

HRID 594956Notes

Reaction equation

HRID 594956 reaction equation
[O:1]1[C@H:3]2[C:4]3[C:5]([O:17][C:18]([CH3:20])([CH3:19])[C@:2]12O)=[CH:6][C:7]1[C:8]([CH3:16])=[CH:9][C:10]([CH2:14][OH:15])=[N:11][C:12]=1[CH:13]=3.[C:22]1([CH2:28][CH2:29][NH2:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)CC>[OH:15][CH2:14][C:10]1[CH:9]=[C:8]([CH3:16])[C:7]2[CH:6]=[C:5]3[O:17][C:18]([CH3:19])([CH3:20])[C@H:2]([OH:1])[C@@H:3]([NH:30][CH2:29][CH2:28][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:4]3=[CH:13][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 86662986HCID 86662986, compound

Product 1

HCID 49801658HCID 49801658, compoundYield 125.8%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To a liquid mixture of 7.98 g (29.4 mmol) of the obtained (3R,4S)-3,4-epoxy-7-hydroxymethyl-2,2,9-trimethyl-3,4-dihydro-2H-pyrano[2,3-g]quinolin-3-ol and 16.07 g of 1-propanol, 4.30 g (35.5 mmol, 1.2 equivalent) of 2-phenylethylamine was added and the resultant mixture was heated and refluxed for 5 hours. The solvent was distilled off to produce 14.52 g of (3R,4S)-7-hydroxymethyl-2,2,9-trimethyl-4-(phenethylamino)-3,4-dihydro-2H-pyrano[2,3-g]quinolin-3-ol as a brown oily substance.

Workup

  1. additionwas added
  2. temperaturerefluxed for 5 hours
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-26482518ac3745d8965088404414059e
Source dataset
uspto-grants-2016_01
Patent number
US09242992B2

Reaction notes

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