Pyridine → HCID 178522687, compound

HRID 483604Notes

Reaction equation

HRID 483604 reaction equation
[C:1]([C:4]1[CH:34]=[CH:33][C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([O:18][CH:19]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1)(O)=[O:2].C(Cl)(=O)C(Cl)=O.[NH2:41][C:42]1[NH:46][N:45]=[N:44][N:43]=1.N1C=CC=CC=1>ClCCl>[NH:43]1[C:42]([NH:41][C:1]([C:4]2[CH:34]=[CH:33][C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([O:18][CH:19]([C:26]4[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[CH2:14][CH2:13]3)=[CH:6][CH:5]=2)=[O:2])=[N:46][N:45]=[N:44]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 19753211HCID 19753211, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178522687HCID 178522687, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 0.84 g (1.75 mmol) of 1-[3-(4-carboxyphenoxy)propyl]-4[(4-chlorophenyl)-2-pyridylmethoxy]piperidine dissolved in 8 ml of dichloromethane was added dropwise 1.5 ml of oxalyl chloride under cooling in an ice bath. The mixture was stirred at 0° C. for 0.5 hour and then at room temperature for 0.5 hour, and concentrated under reduced pressure. The residue was added dropwise to a mixed solution of 0.15 g (1.76 mmol) of 5-amino-1,2,3,4-tetrazole dissolved in 10 ml of dichloromethane and 5 ml of pyridine under cooling in an ice bath. After completion of the dropwise addition, the mixture was stirred at 0° C. for 2 hours and then at room temperature for 2 hours, and concentrated under reduced pressure. The residue was applied to silica gel column chromatography using a mixed solvent of chloroform and methanol in a volume ratio of 20:1 and then using a mixed solvent of chloroform, methanol and 28% aqueous ammonia in a volume ratio of 100:10:1 as eluents to obtain 0.54 g (yield: 57%) of 1-{3-{4-[N-(1,2,3,4-tetrazol-5-yl)carbamoyl]phenoxy}propyl}-4-[(4-chlorophenyl)-2-pyridylmethoxy]piperidine as an orange foamy product.

Workup

  1. temperatureunder cooling in an ice bath
  2. waitat room temperature for 0.5 hour
  3. concentrationconcentrated under reduced pressure
  4. additionAfter completion of the dropwise addition
  5. stirringthe mixture was stirred at 0° C. for 2 hours
  6. waitat room temperature for 2 hours
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-809ccdebcedb4f56a83051d68447e094
Source dataset
uspto-grants-1993_07
Patent number
US05225559

Reaction notes

Loading…