Thiomorpholine → 5-Amino-2-(4-thiomorpholinopiperidin-1-yl)benzonitrile

HRID 1744533Notes

Reaction equation

HRID 1744533 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10])([O-])=O.[NH:19]1[CH2:24][CH2:23][S:22][CH2:21][CH2:20]1>>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:17][CH2:16][CH:15]([N:19]3[CH2:24][CH2:23][S:22][CH2:21][CH2:20]3)[CH2:14][CH2:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

3

Reactant 2

HCID 67164ThiomorpholineHCID 222279875-Nitro-2-(4-oxopiperidin-1-yl)benzonitrile

Product 1

HCID 222278795-Amino-2-(4-thiomorpholinopiperidin-1-yl)benzonitrile

Procedure

Reductive amination was conducted according to J. Org. Chem., vol. 55, p. 2552 (1990) using 5-nitro-2-(4-oxopiperidin-1-yl) benzonitrile and thiomorpholine. Then, the nitro group was reduced in the same manner as in Starting Material Synthesis Example 40 to give the title compound, melting point: 138° C.

Workup

  1. customMaterial Synthesis Example 40

Sources & evidence

ORD record
ord-245712189b394e28b389c77769030896
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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