Formaldehyde → 11-{(S)-3-[2-(3-Fluoro-phenyl)-ethyl]-4-methyl-piperazin-1-yl}-3-methyl-5H-dibenzo[b,e][1,4]diazepine

HRID 1350513Notes

Reaction equation

HRID 1350513 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C@@H:10]2[NH:15][CH2:14][CH2:13][N:12]([C:16]3[C:17]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:18]=4[NH:19][C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[N:22]=3)[CH2:11]2)[CH:5]=[CH:6][CH:7]=1.C=O.[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C@@H:10]2[N:15]([CH3:34])[CH2:14][CH2:13][N:12]([C:16]3[C:17]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:18]=4[NH:19][C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[N:22]=3)[CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 5886072011-{(S)-3-[2-(3-Fluoro-phenyl)-ethyl]-piperazin-1-yl}-3-methyl-5H-dibenzo[b,e][1,4]diazepine

Product 1

HCID 5886057811-{(S)-3-[2-(3-Fluoro-phenyl)-ethyl]-4-methyl-piperazin-1-yl}-3-methyl-5H-dibenzo[b,e][1,4]diazepineYield 92%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Combine 11-{(S)-3-[2-(3-fluoro-phenyl)-ethyl]-piperazin-1-yl}-3-methyl-5H-dibenzo[b,e][1,4]diazepine (385.5 mg, 0.93 mmol), formaldehyde (83.0 μL, 1.02 mmol, 37% in water), and 1,2-dichloroethane (30.0 ml). Stir the mixture at ambient temperature for 5 minutes and then add sodium triacetoxyborohydride (295.6 mg, 1.39 mmol). After stirring for 30 minutes at ambient temperature, quench the reaction with saturated sodium bicarbonate. Remove the organic portion and wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using dichloromethane/methanol (90:10) to give 366.2 mg (92%) of the title compound as a yellow foam: mp 63°, dec; mass spectrum (ion spray): m/z=429.3 (M+1).

Workup

  1. stirringAfter stirring for 30 minutes at ambient temperature
  2. customquench
  3. customthe reaction with saturated sodium bicarbonate
  4. customRemove the organic portion
  5. washwash (brine)
  6. dry with materialdry (sodium sulfate)
  7. customPurify the residue on silica gel

Sources & evidence

ORD record
ord-9049378ad7d6486fa0f36d2a5c2f003d
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

Loading…