Chloroacetonitrile → HCID 14349018, compound

HRID 704670Notes

Reaction equation

C(O)(=O)C(O)=O.[F:7][C:8]([F:28])([F:27])[C:9]1[CH:26]=[CH:25][C:12]([O:13][CH:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][NH:16][CH2:15]2)=[CH:11][CH:10]=1.Cl[CH2:30][C:31]#[N:32].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:31]([CH2:30][N:16]1[CH2:15][CH:14]([O:13][C:12]2[CH:25]=[CH:26][C:9]([C:8]([F:7])([F:27])[F:28])=[CH:10][CH:11]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17]1)#[N:32]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine of Example 1 (16 g, 0.052 mole), chloroacetonitrile (8 g, 0.10 mole) and sodium bicarbonate (17 g, 0.20 mole) in DMF (125 ml) was warmed at 70° C. for 2.5 hours. The mixture was concentrated to an oil which was stirred with water and extracted with ethyl acetate. The organic extracts were washed twice with water and dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvent was evaporated to an oil (18 g) which solidified upon triturating with petroleum ether to a solid (16.5 g, 92%, m.p. 125°-129° C.). A sample was recrystallized from hexanes to yield 3-cyanomethyl-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine, m.p. 134°-135° C.

Workup

concentrationThe mixture was concentrated to an oil which
extractionextracted with ethyl acetate
washThe organic extracts were washed twice with water
dry with materialdried (saturated NaCl, anhydrous MgSO4)
filtrationAfter filtering
customthe solvent was evaporated to an oil (18 g) which
customupon triturating with petroleum ether to a solid (16.5 g, 92%, m.p. 125°-129° C.)
customA sample was recrystallized from hexanes

Sources & evidence

ORD record: ord-f8d6a1cc4b2a43589a57497292d94aab
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04988690

Reaction notes

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