Sodium Carbonate → HCID 3029409, compound

HRID 1679996Notes

Reaction equation

HRID 1679996 reaction equation
[OH:1][CH:2]([CH:5]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][NH2:4].[H-].[Na+].Cl[CH2:24][CH2:25]I.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][CH:5]([CH:2]1[O:1][CH2:25][CH2:24][NH:4][CH2:3]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 1364381-Chloro-2-iodoethaneHCID 15572608HCID 15572608, compound

Product 1

HCID 3029409HCID 3029409, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-hydroxy-3-(2-methoxy-phenoxy)-3-phenyl-propylamine (10 g) in anhydrous dimethylformamide (150 ml), 55% NaH (1.75 g) was added at room temperature. After stirring for 1 hour, a solution of 2-chloro-1-iodo-ethane (7 g) in dimethylformamide (50 ml) was added all at one time. The temperature was maintained at 50° C. for 1 hour then Na2CO3 (5.82 g) was added and the whole was maintained at 50° C. for a further 3 hours. The whole was poured into water and extraction made with ethyl acetate. After a standard working up, procedure, 2-[α-(2-methoxy-phenoxy)-benzyl]-morpholine (6.24 g; 57%) was obtained as a transparent oil. HCl m.p. 140°-170° C. All the compounds mentioned in the Examples 17, 19 and 20 were similarly prepared.

Workup

  1. temperaturethe whole was maintained at 50° C. for a further 3 hours

Sources & evidence

ORD record
ord-658612f933904330a79094b3715929a5
Source dataset
uspto-grants-1981_06
Patent number
US04271160

Reaction notes

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