Dichloromethane → 4-{[3-(3-Benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)propyl]amino}benzonitrile

HRID 1743707Notes

Reaction equation

[CH2:1]([N:8]1[CH2:14][CH:13]2[NH:15][CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O[CH2:27][CH2:28][CH2:29][NH:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CN(C=O)C.O>[CH2:1]([N:8]1[CH2:14][CH:13]2[N:15]([CH2:27][CH2:28][CH2:29][NH:30][C:31]3[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=3)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-benzyl-3,8-diazabicyclo[3.2.1]octane (3.63 g, 17.9 mmol; from Preparation B, step (e) above), 3-(4-cyanoanilino)propyl 4-methylbenzenesulfonate (5.93 g, 17.9 mmol; from step (b) above) and potassium carbonate (2.47 g, 17.9 mmol) in dry DMF (85 mL) was stirred at 80° C. for 4 h. The reaction mixture was diluted with water (200 mL) and extracted with ether (4×200 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered and concentrated ill vacuo to give the crude product. Flash chromatography on silica gel eluting with CH2Cl2:CMA (4:1) gave 6.26 g (97%) of the sub-title compound as a yellow oil.

Workup

extractionextracted with ether (4×200 mL)
washThe combined extracts were washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated ill vacuo
customto give the crude product

Sources & evidence

ORD record: ord-6f2a085f5aec4bdfa9bf0b258a5753f1
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07012074B2

Reaction notes

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