Formaldehyde → HCID 136384265, compound

HRID 131428Notes

Reaction equation

HRID 131428 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][C:14]([CH:24]([CH3:26])[CH3:25])=[C:15]([C@@H:16]([C:21]([O-:23])=[O:22])[CH2:17][C:18]([O-:20])=[O:19])[C:9]=3[C:8]([N:27]3[CH2:32][CH2:31][NH:30][CH:29]([CH2:33][CH2:34][O:35][CH3:36])[CH2:28]3)=[N:7][C:6]=2[CH:37]=1.[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>ClCCl.[Cl-].[Na+]>[C:21]([OH:23])(=[O:22])[CH2:16][CH2:17][C:18]([OH:20])=[O:19].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][C:14]([CH:24]([CH3:26])[CH3:25])=[CH:15][C:9]=3[C:8]([N:27]3[CH2:32][CH2:31][N:30]([CH3:38])[C@@H:29]([CH2:33][CH2:34][O:35][CH3:36])[CH2:28]3)=[N:7][C:6]=2[CH:37]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 136388579HCID 136388579, compound

Product 1

HCID 136384265HCID 136384265, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve (S)-8-chloro-2-isopropyl-11-[3-(2-methoxy-ethyl) piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine succinate (0.089 g, 0.22 mmol) in dichloromethane (12 ml). Add sodium triacetoxyborohydride (0.137 g, 0.65 mmol) and formaldehyde (0.013 g, 0.43 mmol, 0.035 g of a 37% aqueous solution) and stir the mixture for two hours at ambient temperature. Dilute the mixture with 50 mL of saturated aqueous sodium chloride and extract three times with dichloromethane. Combine the organic layers, dryover sodium sulfate and remove the solvent under reduced pressure. Purification via flash chromatography, eluting with a mixture of 75% hexanes and 25% chloroform with 1% total volume isopropylamine, gives the free base of the title compound (0.027 g, 0.06 mmol, 29% yield) as a yellow amorphous solid. Convert to the succinate salt as described previously: Mass Spectrum (m/e): 427(M+1); Exact Mass Spec: Calc. 427.2265; Found 427.2279.

Workup

  1. extractionextract three times with dichloromethane
  2. customremove the solvent under reduced pressure
  3. customPurification via flash chromatography
  4. washeluting with a mixture of 75% hexanes and 25% chloroform with 1% total volume isopropylamine

Sources & evidence

ORD record
ord-0cc5cd5028b54156b6d4637cbc257214
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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