Dichloromethane → HCID 66939863, compound

HRID 1038117Notes

Reaction equation

HRID 1038117 reaction equation
[ClH:1].F[C:3]1[CH:12]=[CH:11]C(F)=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2.C(N(C(C)C)CC)(C)C.[Cl:23][CH2:24][C:25](Cl)=[O:26].Cl[CH2:29][Cl:30]>>[Cl:23][CH2:24][C:25]([N:7]1[CH2:6][CH2:5][C:4]2[C:9](=[C:29]([Cl:30])[CH:11]=[CH:12][C:3]=2[Cl:1])[CH2:8]1)=[O:26]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 450740075,8-Difluoro-1,2,3,4-Tetrahydroisoquinoline Hydrochloride

Product 1

HCID 66939863HCID 66939863, compound

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 5,8-di-fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.69 g, 3.36 mmol) in dichloromethane (20 ml) at 0° C. under nitrogen, diisopropylethylamine (1.40 ml, 8.05 mmol) followed by chloroacetyl chloride (0.32 ml, 4.03 mmol) were added. The mixture was stirred at 0° C. for 2 hr. After being quenched with saturated sodium carbonate solution, water and dichloromethane were added. Layers were separated and the separated aqueous layer was extracted with dichloromethane. The combined organic layers were dried (MgSO4), filtered and solvents were removed in vacuum. Column purification [Hexanes-Ethyl acetate, 4:1 (v/v)] gave chloride 1AC (619 mg, 75%) as colourless oil.

Workup

  1. additionwere added
  2. customAfter being quenched with saturated sodium carbonate solution, water and dichloromethane
  3. additionwere added
  4. customLayers were separated
  5. extractionthe separated aqueous layer was extracted with dichloromethane
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. customsolvents were removed in vacuum
  9. customColumn purification [Hexanes-Ethyl acetate, 4:1 (v/v)]

Sources & evidence

ORD record
ord-5735e197b6a5423aaaaf6a411e62d7bf
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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