(Piperazin-1-yl)acetonitrile → {4-[(S)-4-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-piperazin-1-yl}-acetonitrile

HRID 1842018Notes

Reaction equation

HRID 1842018 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C@@H:21]3[O:30][C:25]4=[N:26][CH:27]=[CH:28][CH:29]=[C:24]4[O:23][CH2:22]3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[N:31]1(CC#N)CCN[CH2:33][CH2:32]1.C(OC(N1CCN(CC#N)CC1)=O)(C)(C)C.Cl.C12NC(CC1)CN(C(=O)C)C2>>[O:23]1[C:24]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[O:30][C@@H:21]([C:18]2[CH:19]=[CH:20][C:15]([CH2:14][N:11]3[CH2:12][CH2:13][N:8]([CH2:33][C:32]#[N:31])[CH2:9][CH2:10]3)=[CH:16][CH:17]=2)[CH2:22]1

Participants

5

Reactant 4

HCID 15522031(Piperazin-1-yl)acetonitrileHCID 21936030Tert-butyl 4-(cyanomethyl)piperazine-1-carboxylateHCID 672056821-(3,8-Diaza-bicyclo[3.2.1]oct-3-yl)-ethanone hydrochlorideHCID 866953624-[(S)-4-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 71735412{4-[(S)-4-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-piperazin-1-yl}-acetonitrile

Procedure

Compound 284 is synthesized from Intermediate C and piperazin-1-yl-acetonitrile (prepared from 4-Cyanomethyl-piperazine-1-carboxylic acid tert-butyl ester according to the procedure used to synthesize Intermediate U from U-1) according to General Method F. (LC/MS method 16: ES+ m/z 351.3 [M+H]+, Rt=2.68 min)

Sources & evidence

ORD record
ord-f71454ab77664ab4b083e3b87491b5d9
Source dataset
uspto-grants-2015_02
Patent number
US08946203B2

Reaction notes

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