Ammonia → 2-{[2-(1-Azabicyclo[3.3.0]octan-5-yl)ethyl]amino}benzamide

HRID 260932Notes

Reaction equation

[N:1]12[CH2:8][CH2:7][CH2:6][C:5]1([CH2:9][CH2:10][NH:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15])[CH2:4][CH2:3][CH2:2]2.S(=O)(=O)(O)[OH:21].N>O>[N:1]12[CH2:2][CH2:3][CH2:4][C:5]1([CH2:9][CH2:10][NH:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]([NH2:15])=[O:21])[CH2:6][CH2:7][CH2:8]2

Participants

Conditions

Temperature: -78 °C

Procedure

2-[(1-Azabicyclo[3.3.0]octan-5-yl)ethylamino]benzonitrile (1.34 g, 5.25 mmol) obtained by Example 27 was mixed with concentrated sulfuric acid (48.2 ml) and water 7.5 ml to react the mixture for 2 hours at 110° C. The reaction mixture was cooled to -78° C., neutralized by 25% ammonia solution, extracted by ethyl acetate, washed by water, dried over anhydrous sodium sulfate, concentrated in vacuo, and crystallized from ethyl acetate to afford the desired compound (961 mg, 67.0%).

Workup

customto react the mixture for 2 hours at 110° C
extractionextracted by ethyl acetate
washwashed by water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customcrystallized from ethyl acetate

Sources & evidence

ORD record: ord-76aaf9c120714579b913b5f7060a1d01
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05530138

Reaction notes

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