Hydrochloric Acid → 4-(Benzo[1,3]dioxol-4-yl)-1,2,3,6-tetrahydropyridine hydrochloride

HRID 1909356Notes

Reaction equation

HRID 1909356 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[O:21][CH2:20][O:19][C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:23].O1CCOCC1.C(OC(C)C)(C)C>ClCCl>[ClH:23].[O:19]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)[C:22]=2[O:21][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 312751,4-DioxaneHCID 706568674-Benzo[1,3]dioxol-4-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 706564464-(Benzo[1,3]dioxol-4-yl)-1,2,3,6-tetrahydropyridine hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL flask, 4-Benzo[1,3]dioxol-4-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.22 g, 4.02 mmol was combined with dichloromethane (20 ml) to give a colorless solution. Hydrochloric acid solution, 4M in dioxane (10.1 ml, 40.2 mmol) was added and the reaction mixture was stirred for 4 hours at room temperature. 15 ml of diisoproylether were added and the mixture was stirred for 5 min at 0° C. The precipitate was collected by filtration, washed with 2 ml of diisopropylether and dried to yield the title compound as a white solid (0.820 grs, 85%). MS (ISP) m/z=204.2[(M+H)+].

Workup

  1. customto give a colorless solution
  2. stirringthe mixture was stirred for 5 min at 0° C
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with 2 ml of diisopropylether
  5. customdried

Sources & evidence

ORD record
ord-da8baa663abf4f659c7a3d46fb73bb89
Source dataset
uspto-grants-2013_12
Patent number
US08598357B2

Reaction notes

Loading…