Hydrochloric Acid → 7-(Piperazin-1-yl)-4-(pyrrolidin-1-yl)quinazoline dihydrochloride

HRID 2090813Notes

Reaction equation

HRID 2090813 reaction equation
[N:1]1([C:6]2[C:15]3[C:10](=[CH:11][C:12]([N:16]4[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]4)=[CH:13][CH:14]=3)[N:9]=[CH:8][N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:29]>CO>[ClH:29].[ClH:29].[N:16]1([C:12]2[CH:11]=[C:10]3[C:15]([C:6]([N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[N:7][CH:8]=[N:9]3)=[CH:14][CH:13]=2)[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59746514Tert-butyl 4-(4-(pyrrolidin-1-yl)quinazolin-7-yl)piperazine-1-carboxylate

Product 1

HCID 674553357-(Piperazin-1-yl)-4-(pyrrolidin-1-yl)quinazoline dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-butyl 4-(4-(pyrrolidin-1-yl)quinazolin-7-yl)piperazine-1-carboxylate (B) (130 mg, 0.339 mmol) was dissolved at room temperature in methanol (2 ml), and then hydrogen chloride (2.71 ml, 3.39 mmol, 1.25 M solution in methanol) was added. The reaction mixture was refluxed for 1 h and then stirred for 15 h at room temperature. Concentration in vacuo was carried out, and the residue was taken up in a small amount of ethanol and heated. Diethyl ether was then added, the mixture was cooled in an ice bath, and finally the resulting solid was filtered off.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. concentrationConcentration in vacuo
  3. temperatureheated
  4. additionDiethyl ether was then added
  5. temperaturethe mixture was cooled in an ice bath
  6. filtrationfinally the resulting solid was filtered off

Sources & evidence

ORD record
ord-31c9649b05bf48b4a85014687e177ee0
Source dataset
uspto-grants-2013_05
Patent number
US08435978B2

Reaction notes

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