Formaldehyde → 3-Methyl-11-[4-methyl-(S)-3-phenethyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

HRID 1350511Notes

Reaction equation

HRID 1350511 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]([N:12]3[CH2:17][CH2:16][NH:15][C@@H:14]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:13]3)=[N:10][C:9]3[CH:26]=[CH:27][CH:28]=[CH:29][C:8]=3[NH:7][C:6]=2[CH:30]=1.C=O.[C:33](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]([N:12]3[CH2:17][CH2:16][N:15]([CH3:33])[C@@H:14]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:13]3)=[N:10][C:9]3[CH:26]=[CH:27][CH:28]=[CH:29][C:8]=3[NH:7][C:6]=2[CH:30]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 588606203-Methyl-11-[(S)-3-phenethyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

Product 1

HCID 210935213-Methyl-11-[4-methyl-(S)-3-phenethyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepineYield 85%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Combine 3-methyl-11-[(S)-3-phenethyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine (375.0 mg, 0.95 mmol), formaldehyde (84.4 μL, 1.04 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 (300.6 mg, 1.42 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 329.5 mg (85%) of the title compound as a tan foam: mp 65°, dec; mass spectrum (ion spray): m/z=411.3 (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-f9da51694e334a91bbb912c209a224ed
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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