Dimethylamine → HCID 58497419, compound

HRID 2175185Notes

Reaction equation

HRID 2175185 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[C:8]([CH3:11])[CH:9]=2)[C:4]([CH:13]=O)=[CH:3]1.[CH3:15][NH:16][CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:15][N:16]([CH3:17])[CH2:13][C:4]1[C:5]2[C:10](=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=2[CH3:12])[N:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 534339461,4,6-Trimethyl-1H-indole-3-carbaldehyde

Product 1

HCID 58497419HCID 58497419, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,4,6-trimethyl-1H-indole-3-carbaldehyde (875 mg, 4.7 mmol) in CH2Cl2 (30 mL) and dimethylamine (2.0 M solution in MeOH) (4.7 mL, 9.3 mmol) was added sodium triacetoxyborohydride (NaBH(OAc)3) (2.9 g, 14 mmol) at 0° C. Upon complete addition the cooling bath was removed and the reaction mixture was stirred at room temperature for 48 h. When the reaction was complete, the mixture was diluted with CH2Cl2 and washed with saturated NaHCO3. The layers were separated and the organic phase was dried over MgSO4, filtered and concentrated. The residue was used in the next step of the synthesis without purification.

Workup

  1. additionUpon complete addition the cooling bath
  2. customwas removed
  3. additionthe mixture was diluted with CH2Cl2
  4. washwashed with saturated NaHCO3
  5. customThe layers were separated
  6. dry with materialthe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was used in the next step of the synthesis without purification

Sources & evidence

ORD record
ord-d889cc2827704f0a89eb1f1c70ad2ff3
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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