Benzhydrylamine → HCID 178482705, compound

HRID 1894928Notes

Reaction equation

HRID 1894928 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][C:11]([CH:17]=O)=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCOC(C)=O>[C:27]1([CH:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)/[N:19]=[CH:17]/[C:11]2[CH:10]=[C:9]3[C:14]([CH:15]=[CH:16][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[N:8]3)=[CH:13][CH:12]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 7036BenzhydrylamineHCID 468355462-Phenylquinoline-7-carbaldehyde

Product 1

HCID 178482705HCID 178482705, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

2-Phenylquinoline-7-carbaldehyde (85.00 g, 0.364 mol) and EtOAc (255 mL) were added to a rbf and heated in a 70° C. oil bath. Half of aminodiphenylmethane (70.11 g, 0.38261 mol) was added quickly. After 2 min, a light brown solid precipitated. The reaction was exothermic and the reaction temperature increased to 73° C. The remaining aminodiphenylmethane was then added within 3 min. The reaction temperature decreased to 67° C. slowly. After 30 min, heating was discontinued and the reaction was cooled in an ice bath to about 15° C. The yellow solid was collected by vacuum filtration and dried in vacuo at 45° C. overnight. The title compound was isolated as a yellow solid (115.77 g, 80% yield). 1H NMR (400 MHz, CDCl3) δ ppm 5.69 (s, 1H), 7.21-7.28 (m, 2H), 7.31-7.38 (m, 4H), 7.43-7.50 (m, 5H), 7.50-7.57 (m, 2H), 7.84 (d, J=8.59 Hz, 1H), 7.90 (d, J=8.59 Hz, 1H), 8.13-8.19 (m, 2H), 8.22 (d, J=8.08 Hz, 1H), 8.26 (dd, J=8.46, 1.64 Hz, 1H), 8.37 (s, 1H), 8.65 (s, 1H).

Workup

  1. customa light brown solid precipitated
  2. temperaturethe reaction temperature increased to 73° C
  3. additionThe remaining aminodiphenylmethane was then added within 3 min
  4. customdecreased to 67° C.
  5. waitAfter 30 min
  6. temperatureheating
  7. temperaturethe reaction was cooled in an ice bath to about 15° C
  8. filtrationThe yellow solid was collected by vacuum filtration
  9. customdried in vacuo at 45° C. overnight

Sources & evidence

ORD record
ord-71fa9e28e9494c84bf8662c07b13b71b
Source dataset
uspto-grants-2013_08
Patent number
US08513415B2

Reaction notes

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