1,1-Dichloroethane → HCID 9908868, compound

HRID 1882980Notes

Reaction equation

HRID 1882980 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:24])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:6][CH:7]=1.ClC(Cl)C.[CH:29]1([CH:32]=O)[CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1CCCC1=O.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:24])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][CH:18]2[CH2:19][CH2:20][N:21]([CH2:32][CH:29]3[CH2:31][CH2:30]3)[CH2:22][CH2:23]2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 63651,1-DichloroethaneHCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 21906555HCID 21906555, compound

Product 1

HCID 9908868HCID 9908868, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a small sample of N-(5-chloropyridin-2-yl)-2-(piperidin-4-ylmethylamino)benzamide (0.034 g, 0.1 mmol) weighed out in a 1 mL sealable vial, dichloroethane was added (300 μL), followed by excess of cyclopropane-carboxaldehyde (20 μL, >0.15 mmol) and sodium triacetoxyborohydride (200 μL of a 1.5 M solution in N-methyl-pyrrolidinone). The vial was capped and placed in a shaker at 70° C. overnight. After an additional 24 h at room temperature, methanol was added (400 μL) and the vial was shaken for a few minutes. The reaction mixture was then applied to a 2 g SCX column, washed with methanol (30 mL) and gravity-eluted with 1 N ammonia in methanol (20 mL). The yellow fractions were combined and concentrated in vacuo to a dry residue (0.040 g, >100%), which was identified as the title compound by LC-MS (Method A).

Workup

  1. customThe vial was capped
  2. waitAfter an additional 24 h at room temperature
  3. washwashed with methanol (30 mL)
  4. washgravity-eluted with 1 N ammonia in methanol (20 mL)
  5. concentrationconcentrated in vacuo to a dry residue (0.040 g, >100%), which

Sources & evidence

ORD record
ord-f28508eabce14de38ea0fe8a1cc7aaf7
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

Loading…