Phenethylamine → HCID 66598115, compound

HRID 1798419Notes

Reaction equation

HRID 1798419 reaction equation
S=C1[N:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18](=[O:20])[CH3:19])=[C:13]([O:21][CH3:22])[CH:12]=2)=[O:8])[CH2:5][CH2:4]S1.C(N)C[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[C:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][O:9][C:7](=[O:8])[NH:6][CH2:5][CH2:4][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:12][C:13]=1[O:21][CH3:22])(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 568478684-(Acetyloxy)-3-methoxybenzyl 2-thioxo-1,3-thiazolidine-3-carboxylate

Product 1

HCID 66598115HCID 66598115, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred yellow solution of VII (362.5 mg, 1.062 mmol) in anhydrous THF (10 mL) was added phenethylamine (142 mg, 147 μL, 1.1×1.062 mmol) and then, dropwise, triethylamine (118 mg, 164 μL, 1.1×1.062 mmol). The solution was stirred for 1 hour at room temperature. The colorless solution was then diluted with CH2Cl2 and washed with 1N HCl, distilled water, and saturated NaCl. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate (1:1, v/v) to yield 203 mg (56%) of 12 as a clear light yellow oil: Rf=0.45 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) δ 7.28 (td, 3J=7.4 Hz, 2H), 7.20 (tt, 3J=7.4 Hz, 1H), 7.16 (d, 3J=7.3 Hz, 2H), 6.98 (d, 3J=8.0 Hz, 1H), 6.93 (d, 1H), 6.90 (dd, 3J=8.0 Hz, 1H), 5.04 (s, 2H, CH2O), 4.73 (bs, 1H, NH), 3.81 (s, 3H, OCH3), 3.45 (q, 3J=6.6 Hz, 2H, NCH2), 2.80 (t, 3J=6.9 Hz, 2H, PhCH2) and 2.29 (s, 3H). Exact mass (ESI) calculated for C19H22NO5 [M+H]=344.1492. found 344.1496.

Workup

  1. washwashed with 1N HCl
  2. distillationdistilled water, and saturated NaCl
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ce6c15d317204de7ac6c2a45ae26279d
Source dataset
uspto-grants-2013_01
Patent number
US08343971B2

Reaction notes

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