Dichloromethane → HCID 67283683, compound

HRID 1890391Notes

Reaction equation

HRID 1890391 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[Cl:32]CCl>>[Cl-:32].[F:24][C:21]([F:22])([F:23])[C:17]1[CH:16]=[C:15]([NH:14][CH:11]2[CH2:10][CH2:9][NH2+:8][CH2:13][CH2:12]2)[CH:20]=[CH:19][N:18]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acid2×HCID 67283813HCID 67283813, compound

Product 1

HCID 67283683HCID 67283683, compound

Procedure

To a solution of 4-(2-trifluoromethyl-pyridin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (4.09 g (11.8 mmol) in dichloromethane (20 mL) is added trifluoroacetic acid (10 mL) and the reaction mixture is stirred at room temperature for one hour. More trifluoroacetic acid (2 mL) is added and stirring is continued for 30 minutes. All volatiles are then removed under high vacuum and to the residue is then added a 4 N solution of HCl in dioxane. All volatiles are then removed again and the residue triturated with diethyl ether. The solid is sucked to dryness and taken up with methanol. After evaporation of all volatiles, the residue is again triturated with diethyl ether and after drying under high vacuum, the desired compound is obtained (26% overall yield).

Workup

  1. stirringstirring
  2. waitis continued for 30 minutes
  3. customAll volatiles are then removed under high vacuum and to the residue
  4. additionis then added a 4 N solution of HCl in dioxane
  5. customAll volatiles are then removed again
  6. customthe residue triturated with diethyl ether
  7. customAfter evaporation of all volatiles
  8. customthe residue is again triturated with diethyl ether
  9. customafter drying under high vacuum

Sources & evidence

ORD record
ord-828ff64e4eaa452e827d8637e2925c70
Source dataset
uspto-grants-2013_08
Patent number
US08507474B2

Reaction notes

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