Diisopropylethylamine → HCID 18353746, compound

HRID 430079Notes

Reaction equation

HRID 430079 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH2:5][N:6]1[CH2:11][CH:10]=[CH:9][CH2:8][CH:7]1[CH2:12][CH2:13][NH2:14].Cl[C:20]1[NH:21][C:22]2[C:27]([C:28](=[O:30])[CH:29]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.C(N(C(C)C)CC)(C)C>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH2:5][N:6]1[CH2:11][CH:10]=[CH:9][CH2:8][CH:7]1[CH2:12][CH2:13][NH:14][C:20]1[NH:21][C:22]2[C:27]([C:28](=[O:30])[CH:29]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 183536642-Chloroquinolin-4(1H)-oneHCID 18353721HCID 18353721, compound

Product 1

HCID 18353746HCID 18353746, compound

Conditions

Temperature
110 °C

Procedure

A mixture of 2-[1-(3,4-dichlorobenzyl)-1,2,3,6-tetrahydropyridin-2-yl]ethylamine (284 mg, 1 mmol), 2-chloro-1H-quinolin-4-one (184 mg, 1.03 mmol) and diisopropylethylamine (0.18 mL, 1.03 mmol) was heated at 110° C. After 56 h the mixture was cooled and the residue chromatographed over silica gel eluting with dichloromethane and increasing amounts of methanol containing 10% concentrated aqueous ammonia to yield the title compound as a pink foam. δH (CD3OD) 1.59-1.69 (1H, m), 1.83-2.10 (2H, m), 2.21-2.42 (1H, m), 2.90-3.15 (4H, m), 3.67 (2H, s), 5.55-5.64 (1H, s), 5.66 (1H, s), 5.72-5.87 (1H, m), 7.18-7.58 (6H, m), 8.10 (1H, d, J=6.67 Hz); MS (ES+) 426 (100%) MH+.

Workup

  1. temperatureAfter 56 h the mixture was cooled
  2. customthe residue chromatographed over silica gel eluting with dichloromethane
  3. temperatureincreasing amounts of methanol containing 10% concentrated aqueous ammonia

Sources & evidence

ORD record
ord-7aecc56cb17247f7877a8a66f93b672a
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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