Formaldehyde → HCID 68913049, compound

HRID 887522Notes

Reaction equation

HRID 887522 reaction equation
[CH3:1][C:2]1([CH3:21])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:3]1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:26](C)=O.[Na+]>>[CH3:1][C:2]1([CH3:21])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([CH3:26])[CH2:17][CH2:16]2)[CH2:3]1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 21959634HCID 21959634, compound

Product 1

HCID 68913049HCID 68913049, compound

Procedure

3,3-Dimethyl-1-piperidin-4-ylmethyl-6-nitro-2,3-dihydro-1H-indole was treated with an excess of formaldehyde and NaBH(OAc)3 and stirred overnight at RT. The reaction was quenched with MeOH and concentrated in vacuo. The residue was partitioned between EtOAc and 1N NaOH. The organic layer was removed, washed with brine, dried (Na2SO4), filtered and concentrated to provide the compound.

Workup

  1. customThe reaction was quenched with MeOH
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between EtOAc and 1N NaOH
  4. customThe organic layer was removed
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto provide the compound

Sources & evidence

ORD record
ord-e121f10f57cf48cca206978dd69f7af8
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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