Phenethylamine → HCID 10090547, compound

HRID 2293925Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9](Cl)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:12]1[CH2:16][C@H:15]([OH:17])[C@@H:14]([OH:18])[C@H:13]1[OH:19].[C:20]1([CH2:26][CH2:27][NH2:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCO>[NH2:1][C:2]1[N:10]=[C:9]([NH:28][CH2:27][CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:12]1[CH2:16][C@H:15]([OH:17])[C@@H:14]([OH:18])[C@H:13]1[OH:19]

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of compound 50 (300 mg, 1.05 mmol) in absolute EtOH (10 mL) was added phenylethylamine (300 mg, 2.45 mmol). This mixture was heated at 90° C. for 3 days. The solvent was removed by rotary evaporation, and the residue was subjected to column chromatography on silica gel (CH2Cl2 -MeOH) to give compound 51 (272 mg, 70%) as a yellow solid: mp. 200° C. (dec.); 1H NMR (DMSO-d6) δ 1.77-1.90 (m, 1 H, H-5'), 2.50-2.60 (m, 1 H, H-5'), 2.8 (m, 4 H, 2 x CH2), 3.75 (m, 1 H, H-2'), 3.89 (m, 1 H, H-1'), 4.40-4.52 (m, 1 H, H-3'), 4.62-4.81 (m, 1 H, H-4'), 4.87 (d, 1 H, J=3.6 Hz, OH), 5.01 (d, 1 H, J=6.6 Hz, OH), 5.36 (d, 1 H, J=4.8 Hz, OH), 7.22 (s, 2 H, NH2), 7.48 (m, 5 H, Ph), 8.48 (s, 1 H, H-8).

Workup

customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record: ord-0e04a59048f8440d89a9136c9aea1424
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688774

Reaction notes

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