(+/-)-3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl)amino]propanenitrile → HCID 18694178, compound

HRID 399924Notes

Reaction equation

HRID 399924 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH2:11][N:12]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:13][CH2:14][C:15]#[N:16].[H][H]>CO.[Ni]>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH2:11][N:12]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:13][CH2:14][CH2:15][NH2:16]

Participants

5

Reactant 2

HCID 18694181(+/-)-3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl)amino]propanenitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 18694178HCID 18694178, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of (±)-3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl)amino]propanenitrile (0.069 mol) in methanol (250 ml) was hydrogenated with Raney nickel (5 g) as a catalyst. After uptake of hydrogen (2 eq.), the catalyst was filtered off and the filtrate was evaporated, yielding 20 g (94% crude residue) of (±)-N-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N-(phenylmethyl)-1,3-propanediamine (interm. 4-c).

Workup

  1. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-98f0972430164d41bf52445ddeaf5867
Source dataset
uspto-grants-1998_10
Patent number
US05824682

Reaction notes

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