Hydrochloric Acid → 4-Aminopiperidyl 4-{[4-(4-chlorophenyl)pyrimidin-2-yl]amino}phenyl ketone hydrochloride

HRID 33452Notes

Reaction equation

HRID 33452 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[N:29]=[C:28]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=4)[CH:27]=[CH:26][N:25]=3)=[CH:19][CH:18]=2)=[O:16])[CH2:11][CH2:10]1)=O)(C)(C)C.Cl>CCO>[ClH:36].[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([C:28]2[CH:27]=[CH:26][N:25]=[C:24]([NH:23][C:20]3[CH:19]=[CH:18][C:17]([C:15]([N:12]4[CH2:11][CH2:10][CH:9]([NH2:8])[CH2:14][CH2:13]4)=[O:16])=[CH:22][CH:21]=3)[N:29]=2)=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58716577HCID 58716577, compound

Product 1

HCID 219060194-Aminopiperidyl 4-{[4-(4-chlorophenyl)pyrimidin-2-yl]amino}phenyl ketone hydrochlorideYield 171.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(tert-Butoxy)-N-{1-[(4-{[4-(4-chlorophenyl)pyrimidin-2-yl]amino}phenyl)carbonyl](4-piperidyl)}carboxamide (4.00 g, 7.87 mmol) was stirred in 50 mL EtOH followed by addition of anhydrous HCl gas. The reaction was stirred for 30 min. then concentrated down to a residue. To this was added a small amount of EtOH followed by dilution with ether. A yellow solid formed which was filtered and dried to give 3.00 grams of 4-aminopiperidyl 4-{[4-(4-chlorophenyl)pyrimidin-2-yl]amino}phenyl ketone hydrochloride: HPLC Retention time; 5.89 min. (Method B) M+1; 408.4

Workup

  1. concentrationthen concentrated down to a residue
  2. additionTo this was added a small amount of EtOH
  3. customA yellow solid formed which
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-194571c77ada4c7c901a8187417705c3
Source dataset
uspto-grants-2008_09
Patent number
US07429599B2

Reaction notes

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