Aniline → 1-[(3,4-Dihydro-2-naphthalenyl)methyl]-4-anilino isonipecotonitrile

HRID 2072477Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[CH2:11][N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C-:26]#[N:27].[K+].[OH-].[NH4+]>O.C(O)(=O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[CH2:11][N:12]1[CH2:17][CH2:16][C:15]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:26]#[N:27])[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of 1-[(3,4-dihydro-2-naphthalenyl)methyl]-4-oxopiperidine (24.0 g), aniline (9.3 g), and glacial acetic acid (70 ml) is cooled to 30° C and heated with a solution of potassium cyanide (7.2 g) in water (20 ml). The resulting mixture is stirred for 16 hours at room temperature. The reaction mixture is poured into aqueous ammonium hydroxide and extracted with chloroform. The organic solution is dried and concentrated to give the title compound.

Workup

extractionextracted with chloroform
customThe organic solution is dried
concentrationconcentrated

Sources & evidence

ORD record: ord-f55c85131ed143b1bd9418451088a7dd
Source dataset: uspto-grants-1977_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04051248

Reaction notes

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