Trifluoroacetic acid → HCID 90218727, compound

HRID 1480431Notes

Reaction equation

HRID 1480431 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)=[O:19])[CH2:14][CH2:13]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)=[O:19])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86722718HCID 86722718, compound

Product 1

HCID 90218727HCID 90218727, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3,5-dichlorobenzyl 4-(3-(tert-butoxycarbonylamino)propyl)piperazine-1-carboxylate (step 1) (438 mg, 0.981 mmol) in DCM (6 ml) was added TFA (3 ml, 38.9 mmol). The resulting solution was stirred for 1 hr and then concentrated under reduced pressure. The residue was basified with saturated sodium bicarbonate solution (50 ml) and extracted with EtOAc (2×100 ml). The combined extracts were dried (MgSO4) and concentrated to give 3,5-dichlorobenzyl 4-(3-aminopropyl)piperazine-1-carboxylate as a tan crystalline solid;

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with EtOAc (2×100 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b34ec92975364d33b0cf53dc43eebd4b
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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