Thionyl Chloride → 5-(2-Chloroethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride

HRID 1375033Notes

Reaction equation

HRID 1375033 reaction equation
O[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][C:7]2[S:10][CH:11]=[CH:12][C:6]=2[CH2:5]1.S(Cl)([Cl:15])=O>ClCCl>[ClH:15].[Cl:15][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][C:7]2[S:10][CH:11]=[CH:12][C:6]=2[CH2:5]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 179638695-(2-Hydroxyethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Product 1

HCID 179642775-(2-Chloroethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5-(2-hydroxyethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (0.49 g) in dichloromethane (20 ml) was added dropwise thionyl chloride (0.39 ml). The mixture was stirred at 40° C. for 1.5 hours. After the mixture was evaporated under reduced pressure, the residue was triturated with diisopropyl ether. The resulting powder was collected by filtration, washed with diisopropyl ether and dried in vacuo to give 5-(2-chloroethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (0.44 g).

Workup

  1. customAfter the mixture was evaporated under reduced pressure
  2. customthe residue was triturated with diisopropyl ether
  3. filtrationThe resulting powder was collected by filtration
  4. washwashed with diisopropyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-cb91967144034c0f9a44111fbce2ecb7
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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