Hydrochloric Acid → 6-[2-(4-Piperidyl)ethyl]-[1,3]dioxolo[4,5-f]isoindole-5,7-dione hydrochloride

HRID 528502Notes

Reaction equation

HRID 528502 reaction equation
[O:1]=[C:2]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][O:13][C:7]3=[CH:6][C:5]=2[C:4](=[O:14])[N:3]1[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]1.[ClH:30]>C(OCC)(=O)C>[ClH:30].[NH:20]1[CH2:21][CH2:22][CH:17]([CH2:16][CH2:15][N:3]2[C:4](=[O:14])[C:5]3[CH:6]=[C:7]4[O:13][CH2:12][O:11][C:8]4=[CH:9][C:10]=3[C:2]2=[O:1])[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90064408Tert-butyl 4-[2-(5,7-dioxo-[1,3]dioxolo[4,5-f]isoindol-6-yl) ethyl]piperidine-1-carboxylate

Product 1

HCID 1180573866-[2-(4-Piperidyl)ethyl]-[1,3]dioxolo[4,5-f]isoindole-5,7-dione hydrochlorideYield 92.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 500 ml reaction vessel, 20 g (0.05 mol) compound XI and 400 ml 10% solution of hydrogen chloride in ethyl acetate were added, the reaction was kept at room temperature for 2 h, filtrated, washed, oven-dried, and 15.5 g compound II-1 was obtained, with yield of 92.3%. 1H NMR (D2O): δ 1.40-1.64 (m, 5H), 2.02 (d, 2H, J=13.4 Hz), 2.96-3.03 (m, 2H), 3.45-3.50 (m, 4H), 6.12 (s, 2H), 6.79 (s, 2H); MS (ESI): m/z 303 [M−Cl]+.

Workup

  1. additionwere added
  2. filtrationfiltrated
  3. washwashed
  4. customoven-dried

Sources & evidence

ORD record
ord-d767bf1242ae41ed8a328a70f0a6a65b
Source dataset
uspto-grants-2016_05
Patent number
US09346818B2

Reaction notes

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