Diethylamine → 3-cyclopentyloxy-N,N-diethyl-4-methoxy-benzamide

HRID 2300044Notes

Reaction equation

HRID 2300044 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH:6]1([O:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[C:15](Cl)=[O:16])[CH2:10][CH2:9][CH2:8][CH2:7]1>C(Cl)Cl>[CH:6]1([O:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[C:15]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:16])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 27946003-(Cyclopentyloxy)-4-methoxybenzoyl chloride

Product 1

HCID 185048253-cyclopentyloxy-N,N-diethyl-4-methoxy-benzamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylamine (69.2 g, 0.672 moles) was added dropwise at 5-10° C. to a solution of 3-cyclopentyloxy-4-methoxy benzoyl chloride (57 g, 0.224 moles) obtained as described in example 2, in methylene chloride (250 ml). The mixture was evaporated to dryness, dissolved in ethyl acetate, washed with water, with 2% potassium bisulphate, again with water and sodium bicarbonate, dried on sodium sulphate and brought to dryness. The residue was taken up with petrolatum (250 ml) to give 61.2 g of the title compound (yield: 94%).

Workup

  1. customobtained
  2. customThe mixture was evaporated to dryness
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water, with 2% potassium bisulphate, again with water and sodium bicarbonate
  5. customdried on sodium sulphate

Sources & evidence

ORD record
ord-7a55878becb84043975898e6c7891d60
Source dataset
uspto-grants-2002_12
Patent number
US06498160B2

Reaction notes

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