Dimethylamine → HCID 22638707, compound

HRID 1836662Notes

Reaction equation

HRID 1836662 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]3[CH2:12][CH:11]3[CH:13]=O)[CH:8]=2)[CH:3]=[CH:2]1.[CH3:15][NH:16][CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]3[CH2:12][CH:11]3[CH2:13][N:16]([CH3:17])[CH3:15])[CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22638808HCID 22638808, compound

Product 1

HCID 22638707HCID 22638707, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude 2-(1H-indol-6-yl)-cyclopropanecarbaldehyde was dissolved in methanol at room temperature with stirring. Dimethylamine (1M solution in THF, 20.00 mL, 20.00 mmol) was added followed by sodium triacetoxyborohydride (4.24 g, 20.00 mmol) After 15 h of stirring at room temperature, the solution was concentrated to dryness in vacuo. The residue was then partitioned between methylene chloride and 1 N NaOH solution. The layers were separated, and the organic layer dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude amine was purified by flash chromatography (50% MeOH/EtOAc) to give [2-(1H-indol-6-yl)-cyclopropylmethyl]-dimethyl-amine as a yellow solid (0.62 g, 74% for the two reactions). 1H NMR (CDCl3): δ8.61 (bs, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.08 (t, J=2.7 Hz, 1H), 7.06 (s, 1H), 6.86 (dd, J=11.4, 1.8 Hz, 1H), 6.47 (m, 1H), 2.51 (m, 1H), 2.35 (s, 7H), 1.85 (m, 1H), 0.99 (m, 1H), and 0.85 (m, 1H); LCMS: MH+: 215.16, 78% AP.

Workup

  1. stirringof stirring at room temperature
  2. concentrationthe solution was concentrated to dryness in vacuo
  3. customThe residue was then partitioned between methylene chloride and 1 N NaOH solution
  4. customThe layers were separated
  5. dry with materialthe organic layer dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude amine was purified by flash chromatography (50% MeOH/EtOAc)

Sources & evidence

ORD record
ord-a094b9894b30416fa7f7509191482838
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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