Formamide → 8-[(3,4-Dihydro-2-naphthalenyl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

HRID 2072472Notes

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[CH2:20][CH2:19][C:15]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]([NH2:18])=[O:17])[CH2:14][CH2:13]1.[CH:28](N)=O.C(OCC)(=O)C>O>[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[CH2:20][CH2:19][C:15]2([N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:28][NH:18][C:16]2=[O:17])[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 1-[(3,4-dihydro-2-naphthalenyl)methyl]-4-anilino isonipecotamide (5.0 g) and formamide (18 g) is heated for 12 hours at 170° C. The reaction mixture is cooled, diluted with water (100 ml), and extracted with chloroform. The chloroform solution is dried over sodium sulfate and concentrated to give crude product. Trituration with ethyl acetate produces the title compound.

Workup

temperatureThe reaction mixture is cooled
extractionextracted with chloroform
dry with materialThe chloroform solution is dried over sodium sulfate
concentrationconcentrated
customto give crude product

Sources & evidence

ORD record: ord-9d18760453b047a1b98f888caa04b72a
Source dataset: uspto-grants-1977_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04051248

Reaction notes

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