Sodium Hydroxide → HCID 11770665, compound

HRID 445317Notes

Reaction equation

HRID 445317 reaction equation
FC(F)(F)S(O)(=O)=O.[Cl:9][C:10]1[CH:25]=[CH:24][C:13]([CH:14]=[N:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1.[OH-].[Na+]>>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH:14]2[C:19]3[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][CH2:16][NH:15]2)=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 592516HCID 592516, compound

Product 1

HCID 11770665HCID 11770665, compound

Conditions

Temperature
120 °C

Procedure

To a solution of trifluoromethanesulfonic acid (15.3 mL, 173 mmol) at 0° C. was added N-(4-chlorobenzylidene)-2-phenylethanamine (3.38 g) and the reaction was heated to 120° C. and stirred 17 h under N2. The reaction was poured into ice water (100 mL) and basisified with 5N NaOH (45 mL). The aqueous layer was extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with saturated NaCl (100 mL), dried (MgSO4) and concentrated to give a yellow/brown oil. The residue was purified by ISCO (120 g SiO2, 0-50% EtOAc/hexane) to give 1-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline as a tan solid.

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2 (3×100 mL)
  2. washThe combined organic layers were washed with saturated NaCl (100 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a yellow/brown oil
  6. customThe residue was purified by ISCO (120 g SiO2, 0-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-5e2cbdec4ffd410d8ed6e32ec61015f3
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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