Phenethylamine → Ammonia

HRID 843171Notes

Reaction equation

HRID 843171 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH:20][CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:23][CH2:22]3)[C:9]=2[C:10]=1[CH3:11])=O)C.[CH2:34]([NH2:42])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(OCC)(=O)C>[NH3:20].[CH2:34]([NH:42][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH:20][CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:23][CH2:22]3)[C:9]=2[C:10]=1[CH3:11])=[O:3])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 2

HCID 1001PhenethylamineHCID 53662796HCID 53662796, compound

Product 2

HCID 222AmmoniaYield 25%HCID 53928116HCID 53928116, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 4-(3-(1-benzyl-piperidin-4-ylamino)-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (the compound in Example 100, 15 mg) and phenethylamine (50 μl) was heated at 170° C. for four hours. The reaction mixture was dissolved in ethyl acetate and washed with saturated ammonium chloride solution and water. The organic solvent was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by preparative thin layer chromatography (using dichloromethane:MeOH:ammonia solution (25-28%)=10:1:0.2 as a developing solvent) to give 4-[3-(1-benzyl-piperidin-4-ylamino)-propoxy]-3-methyl-benzofuran-2-carboxylic acid phenethyl-amide (9 mg) as a colorless oil. EI-MS: m/z 525 (M+); 1H-NMR (CDCl3): δ 1.41 (2H, m), 1.85-2.09 (6H, m), 2.51 (1H, m), 2.78 (3H, s), 2.90 (6H, m),3.50 (2H, s), 3.70 (2H, q, J=7 Hz), 4.14 (2H, t, J=6 Hz), 6.61 (1H, d, J=8 Hz), 6.63 (1H, br s), 6.97 (1H, d, J=8 Hz), 7.28 (11H, m).

Workup

  1. washwashed with saturated ammonium chloride solution and water
  2. dry with materialThe organic solvent was dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by preparative thin layer chromatography (

Sources & evidence

ORD record
ord-3ad8ce32a32840cf95bddf232a15257f
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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