Hydrochloric Acid → HCID 9905121, compound

HRID 1068150Notes

Reaction equation

HRID 1068150 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:5].Cl.[CH:25](OC)(OC)OC>>[CH2:13]([N:10]1[CH2:9][CH2:8][CH:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:1]=[CH:25]2)[CH2:12][CH2:11]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 13060622HCID 13060622, compound

Product 1

HCID 9905121HCID 9905121, compound

Procedure

To a solution of 200 mg 2-amino-N-(1-benzyl-piperidin-4-yl)benzamide (from Step A) in 5 mL of trimethyl orthoformate was added 0.2 mL of concentrated HCl. After stinring at 85° C. for 14 hours, the reaction was cooled to room temperature. The reaction mixture was partitioned betweem EtOAc and aqueous sodium bicarbonate. Aqueous phase was extracted with EtOAc (3×). The combined organic phases were washed with brine and dried over anhydrous MgSO4. Concentration under reduced pressure afforded 120 mg of the title compound as a viscous oil.

Workup

  1. customThe reaction mixture was partitioned betweem EtOAc and aqueous sodium bicarbonate
  2. extractionAqueous phase was extracted with EtOAc (3×)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-26c73784599b4199ae28501adce16a62
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

Loading…