Hydrochloric Acid → N1-(4-Chlorobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl]-4-hydroxy-1,2-benzenediamine

HRID 395818Notes

Reaction equation

HRID 395818 reaction equation
[Cl:1][C:2]1[CH:41]=[CH:40][C:5]([C:6]([NH:8][C:9]2[C:10]([NH:23][C:24]([O:26][CH:27]([CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)=[O:25])=[CH:11][C:12]([O:15][Si](C(C)(C)C)(C)C)=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[C:10]([NH:23][C:24]([O:26][CH:27]([CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[C:28]3[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=3)=[O:25])=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[O:7])=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86585765N1-(4-chlorobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbony)-4-(tert-butyldimethylsilyloxy)-1,2-benzenediamine

Product 1

HCID 86585764N1-(4-Chlorobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl]-4-hydroxy-1,2-benzenediamineYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N1-(4-chlorobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbony]-4-(tert-butyldimethylsilyloxy)-1,2-benzenediamine (97 mg, 0.16 mmol) in tetrahydrofuran (2 mL) was treated with 5 N aqueous hydrochloric acid (0.5 mL) and allowed to stand at ambient temperature for 18 h. Volatile solvents were removed in vacuo and the residue diluted with dilute sodium hydrogen carbonate solution, hexane, and methylene chloride. The mixture was sonicated 5 min then filtered. The resultant material was vacuum dried to yield 48 mg (61%) of the title compound as a white solid.

Workup

  1. customVolatile solvents were removed in vacuo
  2. additionthe residue diluted with dilute sodium hydrogen carbonate solution, hexane, and methylene chloride
  3. customThe mixture was sonicated 5 min
  4. filtrationthen filtered
  5. customdried

Sources & evidence

ORD record
ord-cb6df59929924d82ab614177afe2f028
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

Loading…