Trifluoroacetic acid → 3,5-Dichlorobenzyl 2-(2-aminoethyl)morpholine-4-carboxylate

HRID 1480381Notes

Reaction equation

HRID 1480381 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH:11]1[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)=[O:18])[CH2:12]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][CH:11]1[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)=[O:18])[CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867226343,5-Dichlorobenzyl 2-(2-((tert-butoxycarbonyl)amino)ethyl)morpholine-4-carboxylate

Product 1

HCID 867226353,5-Dichlorobenzyl 2-(2-aminoethyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising of 3,5-dichlorobenzyl 2-(2-((tert-butoxycarbonyl)amino)ethyl)morpholine-4-carboxylate (step 1)(500 mg, 1.154 mmol) and trifluoroacetic acid (3556 μl, 46.2 mmol) in DCM (3.8 ml) was stirred for 1 hour at room temperature. The resulting mixture was concentrated under reduced pressure and the crude product was diluted with EtOAc. The mixture was washed with sat. NaHCO3 and the organic portion was separated, dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound;

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. additionthe crude product was diluted with EtOAc
  3. washThe mixture was washed with sat. NaHCO3
  4. customthe organic portion was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5edabf7675c446e98a97320ff952a1c5
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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