Trifluoroacetic acid → HCID 18794222, compound

HRID 1004045Notes

Reaction equation

HRID 1004045 reaction equation
[CH3:1][C:2]1[NH:16][CH2:15][CH2:14][C:4]2=[C:5]3[C:10](=[N:11][C:3]=12)[CH:9]=[CH:8][C:7]([O:12][CH3:13])=[CH:6]3.[C:17](O)([C:19]([F:22])([F:21])[F:20])=[O:18]>C(N(CC)CC)C>[CH2:1]=[C:2]1[C:3]2[NH:11][C:10]3[C:5](=[CH:6][C:7]([O:12][CH3:13])=[CH:8][CH:9]=3)[C:4]=2[CH2:14][CH2:15][N:16]1[C:17](=[O:18])[C:19]([F:22])([F:21])[F:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178487038HCID 178487038, compound

Product 1

HCID 18794222HCID 18794222, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 10-methoxyharmalan (40 mg) in triethylamine (1 ml) is added TFA (2.2 eq). After reaction for 15 min. at 0° C., the mixture is hydrolysed and extracted with CH2Cl2. The crude product is then chromatographed on a preparative plate (eluent: CH2Cl2). 1-Methylene-2-trifluoroacetyl-6-methoxy-1,2,3,4-tetra-hydro-β-carboline is recovered (yield: 20%).

Workup

  1. customAfter reaction for 15 min. at 0° C.
  2. extractionextracted with CH2Cl2
  3. customThe crude product is then chromatographed on a preparative plate (eluent: CH2Cl2)
  4. custom1-Methylene-2-trifluoroacetyl-6-methoxy-1,2,3,4-tetra-hydro-β-carboline is recovered (yield: 20%)

Sources & evidence

ORD record
ord-a539d09935db42fb9cac7bada0e57245
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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