Hydrogen chloride-ethyl acetate → 1-(10-Azatricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien4-yl)-1-ethanone hydrochloride

HRID 10102Notes

Reaction equation

HRID 10102 reaction equation
C(OC([N:8]1[CH2:18][CH:17]2[CH2:19][CH:10]([C:11]3[CH:12]=[CH:13][C:14]([C:20](=[O:22])[CH3:21])=[CH:15][C:16]=32)[CH2:9]1)=O)(C)(C)C.C(OCC)(=O)C.[ClH:29]>>[ClH:29].[CH:17]12[CH2:19][CH:10]([CH2:9][NH:8][CH2:18]1)[C:11]1[CH:12]=[CH:13][C:14]([C:20](=[O:22])[CH3:21])=[CH:15][C:16]2=1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 544919524-Acetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10carboxylic acid tert-butyl ester

Product 1

HCID 218646921-(10-Azatricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien4-yl)-1-ethanone hydrochloride

Conditions

Temperature
70 °C

Procedure

4-Acetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester (190 mg, 0.63 mmol) was treated with excess 3N HCl ethyl acetate and warmed to 70° C. for 1 hour then concentrated and dissolved in a minimum of methanol. The resulting solution was saturated with Et2O and stirred. After 18 hours the white crystalline product was collected by filtration (81 mg, 54%). 1H NMR (400 MHz, DMSO-d6) δ 9.75 (br s, NH), 7.89 (s, 1H), 7.88 (d, J=8.0 Hz, 1H), 7.74 (br s, NH), 7.44 (d, J=8.0 Hz, 1H), 3.33 (br s, 2H), 3.22 (br s, 2H), 3.00 (br m, 2H), 2.54 (s, 3H), 2.17 (m, 1H), 2.02 (d, J=11.0 Hz, 1H). GCMS m/e 201 (M+). M.p. 198–202° C.

Workup

  1. concentrationthen concentrated
  2. dissolutiondissolved in a minimum of methanol
  3. filtrationAfter 18 hours the white crystalline product was collected by filtration (81 mg, 54%)

Sources & evidence

ORD record
ord-b60e3c5ebb754101980b3f930fd4d1c7
Source dataset
uspto-grants-2006_08
Patent number
US07091372B2

Reaction notes

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