Trifluoroacetic acid → Trifluoroacetic acid--3-aminopiperidine-2,6-dione (1/1)

HRID 1036657Notes

Reaction equation

HRID 1036657 reaction equation
[O:1]=[C:2]1[CH:7]([NH:8]C(OC(C)(C)C)=O)[CH2:6][CH2:5][C:4](=[O:16])[NH:3]1.[C:17]([OH:23])([C:19]([F:22])([F:21])[F:20])=[O:18]>C(Cl)Cl>[F:20][C:19]([F:22])([F:21])[C:17]([OH:23])=[O:18].[NH2:8][CH:7]1[CH2:6][CH2:5][C:4](=[O:16])[NH:3][C:2]1=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11310728tert-Butyl (2,6-dioxopiperidin-3-yl)carbamate

Product 1

HCID 53447112Trifluoroacetic acid--3-aminopiperidine-2,6-dione (1/1)Yield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-Dioxo-3-aminopiperidine trifluoroacetate (4) was prepared and isolated as follows. Compound 3 (59 mg) was suspended in CH2Cl2 (5 mL). CF3COOH (0.5 mL) was added. The reaction solution was stirred at room temperature for 4 h. The solvent was removed to give 4 (62 mg, 99%): 1H NMR (DMSO-d6) δ 11.42 (s, 1H), 8.70 (br, 2H), 4.31 (dd, J=5.4 Hz, J=13 Hz), 2.88-2.72 (m, 2H), 2.25-2.09 (m, 2H).

Workup

  1. custom2,6-Dioxo-3-aminopiperidine trifluoroacetate (4) was prepared
  2. customisolated
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-79f8a41b42a14a948f83c309244ac1db
Source dataset
uspto-grants-2013_10
Patent number
US08546430B2

Reaction notes

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