Dimethylamine → HCID 59497634, compound

HRID 1747440Notes

Reaction equation

HRID 1747440 reaction equation
[CH:1]([C:3]1[N:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH3:12])=[C:5]([C:13]#[N:14])[CH:4]=1)=O.[CH3:15][NH:16][CH3:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:15][N:16]([CH2:1][C:3]1[N:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH3:12])=[C:5]([C:13]#[N:14])[CH:4]=1)[CH3:17]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 10954201HCID 10954201, compound

Product 1

HCID 59497634HCID 59497634, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-Formyl-5-methyl-indolizine-1-carbonitrile (200 mg, 1.09 mmol) in CH2Cl2 (10 mL) and dimethylamine (2M MeOH solution) (1.09 mL, 2.17 mmol) was added NaBH(OAc)3 (460 mg, 2.17 mmol) at 0° C. Upon complete addition the cooling bath was removed and the reaction mixture was stirred at room temperature for 12 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 purified by CombiFlash with 20% EtOAc in Hexane as the eluent to afford the desirable product 3-Dimethylaminomethyl-5-methyl-indolizine-1-carbonitrile, CAS: 3-Dimethylaminomethyl-5-methyl-indolizine-1-carbonitrile (150 mg, 65%) as a white solid.

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 purified by CombiFlash with 20% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-0137892064c2489e862b52e06b646b41
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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