4-Methylmorpholine → HCID 15511889, compound

HRID 964046Notes

Reaction equation

HRID 964046 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4]1.O[C:14]1C=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20]CC=O.[C-]#N.[K+].C(C1CCC2C(=CC=CC=2)O1)#[N:28].CN1CCOCC1>CN(C=O)C.N1C=CC=CC=1>[N:28]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:20][NH:1][CH2:2][CH:3]2[CH2:12][CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[O:4]2)[CH:14]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 9032Potassium CyanideHCID 104193513-(2-hydroxyphenyl)propanalHCID 112636861-(3,4-dihydro-2H-1-benzopyran-2-yl)methanamineHCID 19079509HCID 19079509, compound

Product 1

HCID 15511889HCID 15511889, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2.8 g 2-aminomethyl-chromane [obtainable by reacting 3-(2-hydroxy-phenyl)-propanal with KCN and subsequent catalytic reduction of the 2-cyano-chromane] and 2.2 g 3-chloromethyl)-pyridine in 250 ml of DMF are stirred together with 1 g N-methyl-morpholine for 12 hours at 20° and worked up in a conventional manner to give N-(3-pyridylmethyl)-N-(2-chromanyl-methyl)-amine. Stirring with 0.5 equivalents of maleic acid in 100 ml ethanol gives the maleate, m.p 163°-164°.

Sources & evidence

ORD record
ord-69522862dc4e4c2983a788c91b6bc58e
Source dataset
uspto-grants-1998_06
Patent number
US05767132

Reaction notes

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