Formaldehyde → (+/-)-3-[3-(1-Methyl-1,2,3,6-tetrahydro-4-pyridyl)-1H-indol-5-yl]-2-amino-1-propanol

HRID 128974Notes

Reaction equation

HRID 128974 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][N+:22]([O-])=O)[CH:18]=3)[NH:13][CH:12]=2)[CH2:7][CH2:6]1.C=O.O>CN(C=O)C>[CH3:4][N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH:21]([NH2:22])[CH2:1][OH:2])[CH:18]=3)[NH:13][CH:12]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 10942334Sodium MethoxideHCID 15233281HCID 15233281, compound

Product 1

HCID 15233282(+/-)-3-[3-(1-Methyl-1,2,3,6-tetrahydro-4-pyridyl)-1H-indol-5-yl]-2-amino-1-propanolYield 56.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium methoxide (0.30 g) was added to a solution of the product from step (d) (1.5 g) in DMF (15 ml) at 0° C. To the resulting solution was added dropwise a suspension of paraformaldehyde (0.19 g) in DMF (20 ml). The resulting mixture was stirred at 0° C. for 1.5 hours, then poured into water and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried and evaporated in vacuo to give a yellow oil which was eluted through a silica column using DCM/EtOH/NH4OH (50:8:1) as eluant to give the desired product as an off-white solid (0.85 g) which was recrystallised from ethanol.

Workup

  1. additionTo the resulting solution was added dropwise
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. customdried
  5. customevaporated in vacuo
  6. customto give a yellow oil which
  7. washwas eluted through a silica column

Sources & evidence

ORD record
ord-593ce3846663414d9bc973b96c9f333d
Source dataset
uspto-grants-1995_11
Patent number
US05466699

Reaction notes

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