2-(3-Fluorophenyl)ethanamine → HCID 10044666, compound

HRID 747547Notes

Reaction equation

HRID 747547 reaction equation
[CH:1]([C:3]1[S:7][C:6]([O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=O.[F:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][NH2:27])[CH:22]=[CH:23][CH:24]=1.C([O-])([O-])OC.[BH4-].[Na+]>CO>[F:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][NH:27][CH2:1][C:3]2[S:7][C:6]([O:8][C:9]3[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=3)=[CH:5][CH:4]=2)[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 5339282-(3-Fluorophenyl)ethanamineHCID 4311764Sodium borohydrideHCID 53629101MethylorthoformateHCID 58677395HCID 58677395, compound

Product 1

HCID 10044666HCID 10044666, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 4-(5-formyl-thiophen-2-yloxy)-benzamide (90 mg, 0.36 mmol) from Example 1, part B, method B, with 2-(3-fluoro-phenyl)-ethylamine (61 mg, 0.44 mmol), methyl orthoformate (0.48 mL) and methanol (0.7 mL). Stir the resulting mixture for 3 hours and then add sodium borohydride in portions. Stir the reactiom misture until the reaction is complete by TLC or HPLC analyses. Then, concentrate to remove the methanol. Partition the resulting residue between H2O (4 mL) and CH2Cl2 (6 ml). Dry the organic layer over sodium sulfate, filter and concentrate. Purify through flash chromatography [CH2Cl2/Ammonia (2.0 M in methanol) 20/1] to provide the title compound. 1H NMR (CDCl3): 7.72 (d, J=8.7 Hz, 2H), 7.21-7.13 (m, 1H), 7.03 (d, J=8.7 Hz, 2H), 6.92-6.80 (m, 3H), 6.56 (d, J=3.6 Hz, 1H), 6.36 (d, J=3.7 Hz, 1H), 5.82 (bs, 2H), 3.83 (s, 2H), 2.87 (t, J=6.5 Hz, 2H), 2.75 (t, J=6.6 Hz, 2H).

Workup

  1. stirringStir the reactiom misture until the reaction
  2. concentrationThen, concentrate
  3. customto remove the methanol
  4. customPartition the resulting residue between H2O (4 mL) and CH2Cl2 (6 ml)
  5. dry with materialDry the organic layer over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify through flash chromatography [CH2Cl2/Ammonia (2.0 M in methanol) 20/1]

Sources & evidence

ORD record
ord-f33dff7be6aa4d208b11bfc225faa7fa
Source dataset
uspto-grants-2008_07
Patent number
US07396943B2

Reaction notes

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