Morpholine → 4-[3-(Biphenyl-2-yloxy)-propyl]-morpholine

HRID 895361Notes

Reaction equation

HRID 895361 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>>[C:7]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[O:5][CH2:4][CH2:3][CH2:2][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 147519462-(3-Bromo-propoxy)-biphenyl

Product 1

HCID 22983264-[3-(Biphenyl-2-yloxy)-propyl]-morpholine

Procedure

2-(3-Bromo-propoxy)-biphenyl (1.0 g) was reacted with morpholine (5 mL) at 50° C. for 1 hour to form 4-[3-(biphenyl-2-yloxy)-propyl]-morpholine. The excess morpholine was evaporated and water was added, followed by extraction with ethyl acetate. Removal of ethyl acetate afforded 900 mg of 4-[3-(biphenyl-2-yloxy)-propyl]-morpholine (t) as an oil which was used without further purification: m/e: 297.17, MS (ES+): 298.2; 1H NMR (500 MHz, CDCl3): 7.8-7.0 (m, 9H), 4.0 (m, 2H), 3.7 (m, 4H), 2.5 (m, 6H) and 1.8 (m, 2H).

Sources & evidence

ORD record
ord-c7235ded73fd44babe275470c524ad6a
Source dataset
uspto-grants-2005_07
Patent number
US06916798B2

Reaction notes

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