Hydrochloric Acid → HCID 86659261, compound

HRID 1803863Notes

Reaction equation

HRID 1803863 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:10][C:9]=1[N:21]([C:33](=[O:38])[C:34]([F:37])([F:36])[F:35])[CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]1)=[O:7])(C)(C)C.[ClH:39].O1CCOCC1>ClCCl>[ClH:39].[CH2:31]([O:30][C:28]([N:25]1[CH2:26][CH2:27][CH:22]([N:21]([C:33](=[O:38])[C:34]([F:37])([F:35])[F:36])[C:9]2[CH:10]=[C:11]([N:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)[CH:12]=[CH:13][C:8]=2[C:6]([OH:7])=[O:5])[CH2:23][CH2:24]1)=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-DioxaneHCID 86659260HCID 86659260, compound

Product 1

HCID 86659261HCID 86659261, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

ethyl 4-{[2-(tert-butoxycarbonyl)-5-(4-methylpiperazin-1-yl)phenyl](trifluoroacetyl)amino}piperidine-1-carboxylate (2.15 g, 3.960 mmol) was dissolved in dry dichloromethane (8 mL) under nitrogen atmosphere. A 4 M solution of HCl in dioxane (9.9 mL, 39.6 mmol, 10 eq) was then added dropwise and the mixture was stirred at room temperature. After 5 hours 5 more equivalents of HCl were added and the reaction was stirred at room temperature overnight. The mixture was evaporated to dryness and stripped twice with DCM. It was then taken up with DCM/dioxane 1:3 and slurried for 1 hour. The solid was filtered, washed with ether and dried under vacuum at 50° C. for 1 hour. 1.78 g of title compound were obtained as a beige powder (86% yield).

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. customThe mixture was evaporated to dryness
  3. filtrationThe solid was filtered
  4. washwashed with ether
  5. customdried under vacuum at 50° C. for 1 hour

Sources & evidence

ORD record
ord-f0e4478fb30b4824b613905ebd0d5eb1
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

Loading…