Benzylaniline → HCID 67213522, compound

HRID 271315Notes

Reaction equation

HRID 271315 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].[N:8]12[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9]1)[C@@H:6]([O:5][C:3](=[O:4])[N:20]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:7]2

Participants

4

Reactant 2

HCID 66028BenzylanilineHCID 14762749HCID 14762749, compound

Product 1

HCID 67213522HCID 67213522, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a suspension of 750 mg (2.58 mmol) of 3-quinuclidyl chloroformate hydrochloride in 20 mL of 1,2-DCE, a solution of 395 mg (2.15 mmol) of N-phenylbenzylamine in 5 mL of 1,2-DCE 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 (SiO2, eluent: CHCl3-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 (CDCl3): 12.30 (s, 1H), 7.20-6.90 (m, 10H), 5.10 (m, 1H), 4.83 (m, 2H), 3.52 (m, 1H), 3.18 (m, 4H), 2.80 (m, 1H), 2.34 (s, 1H), 1.92 (m, 2H), 1.60 (m, 2H).

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 (SiO2, eluent: CHCl3-methanol 10:1)

Sources & evidence

ORD record
ord-8b516b22fee4462c89167ef2feeea7a1
Source dataset
uspto-grants-2008_11
Patent number
US07452904B2

Reaction notes

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