tert-Butyl piperazine-1-carboxylate → 1-(piperazin-1-ylmethyl)-2,3-dihydro-1H-indene-4-carbonitrile

HRID 2173244Notes

Reaction equation

HRID 2173244 reaction equation
[CH:1]([CH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]#[N:13])[C:6]=2[CH2:5][CH2:4]1)=O.[N:14]1(C(OC(C)(C)C)=O)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C(#N)C1C=CC=CC=1>[N:14]1([CH2:1][CH:3]2[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([C:12]#[N:13])[C:6]=3[CH2:5][CH2:4]2)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 595686981-formyl-2,3-dihydro-1H-indene-4-carbonitrile

Product 1

HCID 675170191-(piperazin-1-ylmethyl)-2,3-dihydro-1H-indene-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 7505BenzonitrileSolvent

Procedure

1-(Piperazin-1-ylmethyl)-2,3-dihydro-1H-indene-4-carbonitrile was prepared starting from 1-formyl-2,3-dihydro-1H-indene-4-carbonitrile and tert-butyl piperazine-1-carboxylate in two steps in an analogous fashion to that described for the synthesis of 2-methoxy-4-[2-piperazin-1-yl)ethyl]benzonitrile above. 1H-NMR (400 MHz, MeOD) δ ppm 7.68 (d, J=7.8 Hz, 1H), 7.58 (d, J=7.8 Hz, 1H), 7.40 (t, J=7.4 Hz, 1H), 3.64˜3.88 (m, 10H), 3.40˜3.46 (m, 1H), 3.20˜3.30 (m, 1H), 3.07˜3.16 (m, 1H), 2.55˜2.70 (m, 1H), 2.10˜2.25 (m, 1H).

Sources & evidence

ORD record
ord-297aa3548f69496084e6a60abe7f087b
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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