Hydrochloric Acid → HCID 17951699, compound

HRID 895508Notes

Reaction equation

HRID 895508 reaction equation
Cl.[Cl:2][C:3]([O:5][CH:6]1[CH:11]2[CH2:12][CH2:13][N:8]([CH2:9][CH2:10]2)[CH2:7]1)=[O:4].[C:14]1([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCCl>[ClH:2].[CH2:21]([N:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3](=[O:4])[O:5][CH:6]1[CH:11]2[CH2:12][CH2:13][N:8]([CH2:9][CH2:10]2)[CH2:7]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66028BenzylanilineHCID 14762748HCID 14762748, compound

Product 1

HCID 17951699HCID 17951699, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a suspension of 750 mg (2.58 mmol) of hydrochloride of 3-quinuclidyl chloroformate in 20 mL of 1,2-dichloroethane, a solution of 395 mg (2.15 mmol) of N-phenylbenzylamine in 5 mL of 1,2-dichloroethane was added dropwise. Once completed the addition, the mixture was refluxed for three hours. The reaction crude was allowed to cool down and the solvent distilled off under reduced pressure. The residue was purified by column chromatography (eluent: chloroform-methanol 10:1) yielding 720 mg (1.95 mmol) of a hygroscopic foam corresponding to the title compound. IR (KBr, cm−1): 3400-3200, 2700-2300, 1700 cm−1. 1H-RMN (δTMS, CDCl3, ppm): 12.30 (1H, s), 7.20-6.90 (10H, m), 5.10 (1H, m), 4.83 (2H, m), 3.52 (1H, m), 3.18 (4H, m), 2.80 (1H, m), 2.34 (1H, s), 1.92 (2H, m), 1.60 (2H, m).

Workup

  1. additionthe addition
  2. temperaturethe mixture was refluxed for three hours
  3. customThe reaction crude
  4. temperatureto cool down
  5. distillationthe solvent distilled off under reduced pressure
  6. customThe residue was purified by column chromatography (eluent: chloroform-methanol 10:1)

Sources & evidence

ORD record
ord-4f9adfc32fc0464fb9b34be73c36b36b
Source dataset
uspto-grants-2005_07
Patent number
US06916828B2

Reaction notes

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