Formaldehyde → HCID 69213371, compound

HRID 131429Notes

Reaction equation

HRID 131429 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[F:9][C:10]1[CH:38]=[CH:37][C:13]2[N:14]=[C:15]([N:27]3[CH2:32][CH2:31][NH:30][C@@H:29]([CH2:33][CH2:34][O:35][CH3:36])[CH2:28]3)[C:16]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:17]=3[NH:18][C:12]=2[CH:11]=1.[C:39](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>ClCCl.[Cl-].[Na+].CO>[NH3:14].[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[F:9][C:10]1[CH:38]=[CH:37][C:13]2[N:14]=[C:15]([N:27]3[CH2:32][CH2:31][N:30]([CH3:39])[C@@H:29]([CH2:33][CH2:34][O:35][CH3:36])[CH2:28]3)[C:16]3[CH:22]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:20]=[CH:19][C:17]=3[NH:18][C:12]=2[CH:11]=1

Participants

8

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69210440HCID 69210440, compound

Product 2

HCID 222AmmoniaYield 10%HCID 69213371HCID 69213371, compoundYield 200%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 5234Sodium ChlorideSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve (S)-7-fluoro-2-trifluoromethyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine succinate (0.048 g, 0.11 mmol) in dichloromethane (6 ml). Add sodium triacetoxyborohydride (0.048 g, 0.23 mmol) and formaldehyde (0.003 g, 0.11 mmol, 0.009 g of a 37% aqueous solution) and stir the mixture for one hour at ambient temperature. Dilute the mixture with 10 ml of saturated aqueous sodium chloride and extract three times with 20 ml of dichloromethane. Combine the organic layers, dry over sodium sulfate and remove the solvent under reduced pressure. Purification via flash chromatography, eluting with a linear gradient starting at 99% dichloromethane: 1% 2M ammonia in methanol, and going to 90% dichloromethane: 10% 2M ammonia in methanol, gives the free base of the title compound (0.049 g, 0.11 mmol, 98% yield), as a yellow amorphous solid. Convert to the succinate salt as described previously: Mass Spectrum (m/e): 437(M+1); Exact Mass Spec: Calc. 437.1965; Found 437.1948.

Workup

  1. extractionextract three times with 20 ml of dichloromethane
  2. dry with materialdry over sodium sulfate
  3. customremove the solvent under reduced pressure
  4. customPurification via flash chromatography
  5. washeluting with a linear gradient

Sources & evidence

ORD record
ord-abf79b47fc034789886b6d302fedd689
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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