Formaldehyde → (S)-2-Trifluoromethyl-11-[3-(3-methoxy-propyl)-4-methyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

HRID 131427Notes

Reaction equation

HRID 131427 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:28]=[CH:27][C:6]2[NH:7][C:8]3[CH:26]=[CH:25][CH:24]=[CH:23][C:9]=3[N:10]=[C:11]([N:12]3[CH2:17][CH2:16][NH:15][C@@H:14]([CH2:18][CH2:19][CH2:20][O:21][CH3:22])[CH2:13]3)[C:5]=2[CH:4]=1.C=O.[C:33](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[F:30][C:2]([F:29])([F:1])[C:3]1[CH:28]=[CH:27][C:6]2[NH:7][C:8]3[CH:26]=[CH:25][CH:24]=[CH:23][C:9]=3[N:10]=[C:11]([N:12]3[CH2:17][CH2:16][N:15]([CH3:33])[C@@H:14]([CH2:18][CH2:19][CH2:20][O:21][CH3:22])[CH2:13]3)[C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 10047618(S)-2-Trifluoromethyl-11-[3-(3-methoxy-propyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

Product 1

HCID 10342762(S)-2-Trifluoromethyl-11-[3-(3-methoxy-propyl)-4-methyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Add (S)-2-trifluoromethyl-11-[3-(3-methoxy-propyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine (0.167 g, 0.399 mmol), formaldehyde (40.8 mg, 0.499 mmol, 37%), and sodium triacetoxyborohydride (0.127 g, 0.598 mmol) in dichloromethane (3 mL). Stir at ambient temperature over night. Dilute the mixture with water and extract with dichloromethane. Wash the organic with brine twice, dry over sodium sulfate, filter, and concentrate under reduced pressure to give crude residue. Purify the residue by flash chromatography, eluting with 2M ammonia in methanol:dichloromethane (5:95) to give the title compound: mass spectrum (m/e):433.08 (M+1).

Workup

  1. extractionextract with dichloromethane
  2. washWash the organic with brine twice
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto give crude residue
  7. customPurify the residue by flash chromatography
  8. washeluting with 2M ammonia in methanol:dichloromethane (5:95)

Sources & evidence

ORD record
ord-d4bb8605b0254a79af39ed717cada7dd
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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