Formaldehyde → HCID 68913049, compound

HRID 238446Notes

Reaction equation

HRID 238446 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-7e3e858363764696860006034771fe14
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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