Triethylamine → HCID 22396217, compound

HRID 1070492Notes

Reaction equation

HRID 1070492 reaction equation
C(N(CC)CC)C.Cl.Cl.[NH:10]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[N:18]=2)[CH2:12][CH2:11]1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH:30]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O>[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:30][N:10]1[CH2:11][CH2:12][CH:13]([NH:16][C:17]2[NH:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 227103,4-DichlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69276408HCID 69276408, compound

Product 1

HCID 22396217HCID 22396217, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.223 ml) was added to a stirred suspension of the product from step (ii) (0.2 g) in dimethylformamide. After 5 min 3,4-dichlorobenzaldehyde (0.175 g) then sodium triacetoxyborohydride (0.212 g) was added and the mixture stirred at room temperature for 3 h. The mixture was partitioned between 2M hyrochloric acid and ether, the aqueous layer was basified with aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was dried and evaporated under reduced pressure. The residue was triturated with ethyl acetate/ether and the solid collected. Yield 0.045 g.

Workup

  1. customThe mixture was partitioned between 2M hyrochloric acid and ether
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with ethyl acetate/ether
  6. customthe solid collected

Sources & evidence

ORD record
ord-90751462821e438c8f008215f4e1c101
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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