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

HRID 427668Notes

Reaction equation

HRID 427668 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)C3C=CN=CC=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:41]=[CH:40][C:5]([C:6]([NH:8][C:9]2[C:10]([NH:23][C:24]([O:26][CH2:27][CH:34]3[CH2:39][CH2:38][N:37]([C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)[CH2:36][CH2:35]3)=[O:25])=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=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 21352718N1-(4-Chlorobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-yl-methoxycarbony]-4-hydroxy-1,2-benzenediamineYield 124.8%

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-bdb59f45befa411a98316efb0c8929d0
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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