Trifluoroacetic acid → 3,5-Dichlorobenzyl 4-(aminomethyl)-2-methylpiperidine-1-carboxylate

HRID 1480371Notes

Reaction equation

HRID 1480371 reaction equation
C(OC([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)=[O:17])[CH:12]([CH3:28])[CH2:11]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=2)=[O:17])[CH:12]([CH3:28])[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867226283,5-Dichlorobenzyl 4-(((tert-butoxycarbonyl)amino)methyl)-2-methylpiperidine-1-carboxylate

Product 1

HCID 867226293,5-Dichlorobenzyl 4-(aminomethyl)-2-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising of 3,5-dichlorobenzyl 4-(((tert-butoxycarbonyl)amino)methyl)-2-methylpiperidine-1-carboxylate (step 3) (970 mg, 2.249 mmol) and trifluoroacetic acid (173 μl, 2.249 mmol) in DCM (7.5 ml) was left stirring at room temperature 18 hours. The resulting mixture was loaded on to a 10 g Isolute® SCX-2 cartridge and washed with MeOH. The product was eluted with 2M ammonia in MeOH and the product fractions were concentrated under reduced pressure to afford the title compound;

Workup

  1. washwashed with MeOH
  2. washThe product was eluted with 2M ammonia in MeOH
  3. concentrationthe product fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-a2e0a33bd73d473f8f69c2c74e52e146
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

Loading…