Formaldehyde → HCID 69663924, compound

HRID 2214757Notes

Reaction equation

HRID 2214757 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:21][CH3:22])=[C:10]([N:13]3[CH2:18][C@H:17]([CH3:19])[NH:16][C@H:15]([CH3:20])[CH2:14]3)[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C=O.[BH3-][C:26]#N.[Na+]>CO>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:21][CH3:22])=[C:10]([N:13]3[CH2:18][C@H:17]([CH3:19])[N:16]([CH3:26])[C@H:15]([CH3:20])[CH2:14]3)[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69664906cis-1-Acetyl-6-(3,5-dimethylpiperazin-1-yl)-5-methoxyindoline

Product 1

HCID 69663924HCID 69663924, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of D2 (1.48 g, 4.9 mmole) in MeOH (50 ml) at room temperature under Ar was treated with aqueous formaldehyde (2.4 ml of 37% w/v, 29 mmole), followed by portionwise addition of NaBH3CN (920 mg, 15 mmole). The mixture was stirred at room temperature for 3 h, then concentrated under vacuum and the residue treated with 10% Na2CO3 solution and extracted with DCM. The extract was dried (Na2SO4) and concentrated under vacuum to afford the title compound as a yellow solid (1.4 g, 90%). MH+ 318.

Workup

  1. concentrationconcentrated under vacuum
  2. additionthe residue treated with 10% Na2CO3 solution
  3. extractionextracted with DCM
  4. dry with materialThe extract was dried (Na2SO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8a00b14048ed4a24bb877eb5a22f9568
Source dataset
uspto-grants-2006_09
Patent number
US07109201B2

Reaction notes

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