Triethylamine → HCID 85955915, compound

HRID 1827552Notes

Reaction equation

HRID 1827552 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH:23]1([C:29](Cl)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:29]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:30])=[CH:13][CH:14]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)aniline

Product 1

HCID 85955915HCID 85955915, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (2.15 g, 10.42 mmol) and triethylamine (3.27 mL, 23.4 mmol) in 100 mL methylene chloride at 0° C. was added cyclohexanecarbonyl chloride (1.46 mL, 10.94 mmol), dropwise. The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the layers were separated. The aqueous layer was washed with 50 mL methylene chloride. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated to afford the title compound of Step A. MS 317.2 (M+1)+

Workup

  1. customthe layers were separated
  2. washThe aqueous layer was washed with 50 mL methylene chloride
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9f6d95030f714bef94c8a05f8622c746
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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