Formaldehyde → 6-Fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 416308Notes

Reaction equation

HRID 416308 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][CH:6]([C:8]([OH:10])=[O:9])[NH2:7].[CH2:14]=O>Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:11](=[CH:12][CH:13]=1)[CH2:14][NH:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5]2

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 99763-Fluorophenylalanine

Product 1

HCID 579479416-Fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 3-fluoro-DL-phenylalanine (100 g) in conc. HCl (1.0 L) was added aq. formaldehyde solution (37% wt.; 400 mL). The reaction mixture was heated to 90° C. and stirred for 3.5 h, then cooled to RT and stirred overnight and filtered. The filtrate was concentrated and the residue was combined with the precipitate to give 6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, which was used without further purification. LRMS (M+H+) m/z 196.1.

Workup

  1. temperaturecooled to RT
  2. stirringstirred overnight
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-72519254b5d644d5b777c0101c3c04a0
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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