Thionyl Chloride → HCID 19081348, compound

HRID 963494Notes

Reaction equation

HRID 963494 reaction equation
Cl.O[CH2:3][C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][N:5]=1.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH2:3][C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19081213HCID 19081213, compound

Product 1

HCID 19081348HCID 19081348, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of l-hydroxymethyl-5,6,7,8-tetrahydroisoquinoline hydrochloride (0.42 g) in chloroform (10 ml) was added dropwise a solution of thionyl chloride (1.1 ml) in chloroform (5 ml) at room temperature and heated for 2 hours at ca. 50° C. The reaction mixture was concentrated in vacuo and the residue was taken up with ethyl acetate. The organic layer was washed with saturated sodium carbonate aqueous solution, dried over sodium sulfate, filtered and concentrated in vacuo to give 1-chloromethyl-5,6,7,8-tetrahydroisoquinoline (0.22 g) as a brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washThe organic layer was washed with saturated sodium carbonate aqueous solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-761cc30f04cd4a679876072d97cb9616
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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