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

HRID 131424Notes

Reaction equation

HRID 131424 reaction equation
[CH3:1][C:2]1[CH:26]=[CH:25][C:5]2[NH:6][C:7]3[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=3[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][NH:14][C@@H:13]([CH2:17][CH2:18][O:19][CH3:20])[CH2:12]3)[C:4]=2[CH:3]=1.C=O.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][C:2]1[CH:26]=[CH:25][C:5]2[NH:6][C:7]3[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=3[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH3:29])[C@@H:13]([CH2:17][CH2:18][O:19][CH3:20])[CH2:12]3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 10043488(S)-2-methyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

Product 1

HCID 10090200(S)-2-Methyl-11-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepineYield 89%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Combine (S)-2-methyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine (300.0 mg, 0.86 mmol), formaldehyde (76.4 μL, 0.94 mmol, 37% in water), and 1,2-dichloroethane (28.0 ml) and stir the mixture at ambient temperature for 5 minutes and add sodium triacetoxyborohydride (272.1 mg, 1.28 mmol). After stirring for 30 minutes at ambient temperature, quench the reaction with saturated sodium bicarbonate. Remove the organic portion, extract the aqueous with dichloromethane and combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using dichloromethane/methanol (90:10) to give 260.4 mg (89%) of a yellow foam: mp=60° C., dec; mass spectrum (ion spray): m/z=365.2 (M+1).

Workup

  1. customquench
  2. customthe reaction with saturated sodium bicarbonate
  3. customRemove the organic portion
  4. extractionextract the aqueous with dichloromethane and combine
  5. washwash (brine)
  6. dry with materialdry (sodium sulfate)
  7. customPurify the residue on silica gel

Sources & evidence

ORD record
ord-ceb78179fa2b42db89f686fdff220453
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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