Formaldehyde → 5-Bromo-6-cyclopropylmethoxy-1,2,3,4-tetrahydro-isoquinoline

HRID 523998Notes

Reaction equation

HRID 523998 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:13][CH2:14][NH2:15].C=O.[C:18](O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[C:7]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:13][CH2:14][NH:15][CH2:18]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 840613812-(2-Bromo-3-cyclopropylmethoxy-phenyl)-ethylamine

Product 1

HCID 1189391255-Bromo-6-cyclopropylmethoxy-1,2,3,4-tetrahydro-isoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 40 mg (0.15 mmol) 2-(2-bromo-3-cyclopropylmethoxy-phenyl)-ethylamine (example XXI) and 17 μL (0.22 mmol) formaldehyde (37% solution in water) in 2 mL DCM are added slowly 23 μL (0.30 mmol) TFA and the resulting mixture is stirred at r.t. over night. The reaction mixture is concentrated by evaporation

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation

Sources & evidence

ORD record
ord-928b837a2b4d4ca28d22779747387bb1
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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