Triethylamine → HCID 54552546, compound

HRID 362900Notes

Reaction equation

HRID 362900 reaction equation
O=S(Cl)Cl.[CH3:5][O:6][C:7]1[C:8]([N+:18]([O-:20])=[O:19])=[C:9]([CH:13]=[C:14]([O:16][CH3:17])[CH:15]=1)[C:10]([OH:12])=O.[NH2:21][CH:22]1[CH2:27][CH2:26][N:25]([CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24][CH2:23]1.C(N(CC)CC)C>C(Cl)(Cl)Cl.C1COCC1.CN(C=O)C>[CH3:5][O:6][C:7]1[C:8]([N+:18]([O-:20])=[O:19])=[C:9]([CH:13]=[C:14]([O:16][CH3:17])[CH:15]=1)[C:10]([NH:21][CH:22]1[CH2:27][CH2:26][N:25]([CH:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:24][CH2:23]1)=[O:12]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 7472021HCID 7472021, compoundHCID 128755351-(Diphenylmethyl)-4-piperidinamine

Product 1

HCID 54552546HCID 54552546, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Step 1): A solution of SOCl2 (0.5 ml, 6.6 mmol) in chloroform (10 ml) was added dropwise to a solution of 3,5-dimethoxy-2-nitrobenzoic acid [Bull. Soc. Chim. Fr., 127, 258 (1990)] (1.0 g, 4.4 mmol) and a catalytic amount of DMF in chloroform (20 ml) at room temperature. The reaction mixture was refluxed for 1 hour and then concentrated. The residue was dissolved in THF (10 ml). The THF solution was added dropwise to a solution of 4-amino-1-diphenylmethylpiperidine (1.2 g, 4.4 mmol) and triethylamine (0.5 ml, 6.6 mmol) in THF (20 ml) at 5° C. The mixture was stirred at room temperature for 1 hour and then concentrated. The residue was dissolved in ethyl acetate and washed with water. The organic layer was dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel (10% ethyl acetate in dichloromethane) to give 3,5-dimethoxy-2-nitro-N-(1-diphenylmethylpiperidin-4-yl)benzamide (81.0%): mp 148°-150° C.

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture was refluxed for 1 hour
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in THF (10 ml)
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialThe organic layer was dried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography on silica gel (10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-d60adb7ba0df4aa2bbd7511c9155db18
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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