Trifluoroacetic acid → 4-Amino-1-(2-chloropyrimidin-4-yl)-4-methylpiperidine

HRID 1157Notes

Reaction equation

HRID 1157 reaction equation
C(OC([NH:8][C:9]1([CH3:22])[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[N:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[NH2:8][C:9]1([CH3:22])[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[N:16]=2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 14798Sodium HydroxideHCID 19694924HCID 19694924, compound

Product 1

HCID 196949304-Amino-1-(2-chloropyrimidin-4-yl)-4-methylpiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure described in Example 2 is followed up to the end of step (c). A solution of 6.81 g (0.021 mol) of 4-t-butoxycarbonylamino-1-(2-chloropyrimidin-4-yl)-4-methylpiperidine (step c) in 80 ml of anhydrous methylene chloride is cooled under a nitrogen atmosphere and 16.4 ml of anisole and 83 ml of trifluoroacetic acid are added slowly. The mixture is stirred for 1 hour at room temperature and 80 ml of a 30% solution of NaOH are added slowly. The reaction medium is extracted with methylene chloride and dried over Na2SO4 and the solvent and the anisole are evaporated off under reduced pressure to give 4-amino-1-(2-chloropyrimidin-4-yl)-4-methylpiperidine as the base, which is treated with maleic acid in an ethanol/ethyl ether mixture. The maleate obtained in this way is isolated by filtration (yield 65%, m.p. 125°-126° C.).

Workup

  1. extractionThe reaction medium is extracted with methylene chloride
  2. dry with materialdried over Na2SO4
  3. customthe solvent and the anisole are evaporated off under reduced pressure

Sources & evidence

ORD record
ord-b6be6f155af94436ba0e8bfe5bd8a6cd
Source dataset
uspto-grants-1998_03
Patent number
US05723611

Reaction notes

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