Diethylammonium chloride → HCID 9868790, compound

HRID 1278577Notes

Reaction equation

HRID 1278577 reaction equation
Cl.[CH2:2]([NH:4][CH2:5][CH3:6])[CH3:3].C[Al](C)C.CO[C:13]([C:15]1[CH:16]=[N:17][C:18]([C:21]2([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=3)[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)=[N:19][CH:20]=1)=[O:14]>ClCCCl.C(Cl)Cl>[CH2:2]([N:4]([CH2:5][CH3:6])[C:13]([C:15]1[CH:16]=[N:17][C:18]([C:21]2([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=3)[CH2:22][CH2:23][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:25][CH2:26]2)=[N:19][CH:20]=1)=[O:14])[CH3:3]

Participants

6

Reactant 3

HCID 10197650Diethylammonium chlorideHCID 16682925TrimethylaluminumHCID 70158902HCID 70158902, compound

Product 1

HCID 9868790HCID 9868790, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring suspension of diethyl amine hydrochloride (986 mg, 9.01 mmol) in 1,2-dicloroethane (25 mL) at 0° C. was added a 2.0 M solution of AlMe3 (4.5 mL, 9.01 mmol) dropwise. The resulting mixture stirred at room temperature for 1 hour. (2-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-pyrimidine-5-carboxylic acid methyl ester (750 mg, 1.80 mmol) was added in one portion and the mixture was heated to 85° C. for 16 hours. The reaction was slowly poured into a saturated solution of Rochelle salts (50 mL) and diluted with CH2Cl2 (50 mL). The layers were separated, the aqueous layer was extracted with CH2Cl2 (3×30 mL) and the combined organic layers were dried and concentrated. The crude material was filtered through a plug of silica gel with 5% MeOH/CHCl3, and the resulting solution was concentrated to yield 815 mg (99% yield) of the desired amide. 1HNMR (400 MHz, CDCl3) δ 8.72 (s, 2H), 7.29-7.14 (comp, 6H), 6.97-6.95 (comp, 2H), 6.68-6.66 (comp, 1H), 3.73 (s, 3H), 3.54-3.52 (comp, 2H), 3.39 (s, 2H), 3.27-3.25 (comp, 2H), 2.98-2.95 (comp, 2H), 2.77-2.74 (comp, 2H), 2.34-2.31 (comp, 2H), 2.16-2.02 (comp, 2H), 1.26-1.17 (comp, 6H); MS (M+1) 459.2.

Workup

  1. temperaturethe mixture was heated to 85° C. for 16 hours
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (3×30 mL)
  4. customthe combined organic layers were dried
  5. concentrationconcentrated
  6. filtrationThe crude material was filtered through a plug of silica gel with 5% MeOH/CHCl3
  7. concentrationthe resulting solution was concentrated

Sources & evidence

ORD record
ord-e995de5d336843bcbf467c9e55de4233
Source dataset
uspto-grants-2002_09
Patent number
US06444679B1

Reaction notes

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