Hydrochloric Acid → 3-(3-Aminocyclohexyl)acrylonitrile hydrochloride

HRID 712038Notes

Reaction equation

HRID 712038 reaction equation
[C:1]([CH:3]=[CH:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([NH:11]C(=O)OC(C)(C)C)[CH2:6]1)#[N:2].[ClH:19].O1CCOCC1>C(Cl)Cl>[ClH:19].[NH2:11][CH:7]1[CH2:8][CH2:9][CH2:10][CH:5]([CH:4]=[CH:3][C:1]#[N:2])[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86717491tert-Butyl {3-[2-cyanovinyl]cyclohexyl}carbamate

Product 1

HCID 867174923-(3-Aminocyclohexyl)acrylonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl {3-[2-cyanovinyl]cyclohexyl}carbamate was treated with 4.0 M hydrogen chloride in dioxane (1.6 mL, 6.6 mmol) in methylene chloride (2 mL) at room temperature for 2 h. The mixture was stripped to dryness to give the desired product as a mixture of cis- and trans-isomers. LCMS calculated for C9H15N2 (M+H)+: m/z=151.1. Found: 151.1.

Sources & evidence

ORD record
ord-c11904e96bc848e89009e8fec7ef00e0
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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