Sodium Iodide → 4-(2-(Benzo[b]thiophen-5-yloxy)ethyl)morpholine

HRID 2267463Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]2[S:9][CH:10]=[CH:11][C:7]=2[CH:6]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[I-].[Na+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[S:9]1[CH:10]=[CH:11][C:7]2[CH:6]=[C:5]([O:4][CH2:3][CH2:2][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:13]=[CH:12][C:8]1=2

Participants

Conditions

Temperature: 70 °C

Procedure

5-(2-Chloroethoxy)benzo[b]thiophene (0.25 g, 1.17 mmol) was dissolved in DMF (3 mL) and treated with morpholine (0.205 mL, 2.35 mmol) and sodium iodide (0.035 g, 0.235 mmol). The mixture was heated to 70° C. and stirred overnight. The reaction was cooled down to room temperature and poured into a saturated aqueous solution of sodium bicarbonate (20 mL), which was extracted several times with ethyl acetate. All the organic extracts were combined and washed with a saturated aqueous solution of sodium bicarbonate, water and brine. The ethyl acetate layer was then dried with sodium sulfate and purified by flash chromatography using a gradient of 0 to 8% methanol in dichloromethane to obtain a clear oil. Yield=0.237 g. MS (M+H)+ 264.

Workup

temperatureThe reaction was cooled down to room temperature
extractionwas extracted several times with ethyl acetate
washwashed with a saturated aqueous solution of sodium bicarbonate, water and brine
dry with materialThe ethyl acetate layer was then dried with sodium sulfate
custompurified by flash chromatography
customto obtain a clear oil

Sources & evidence

ORD record: ord-1da37a92dfe944dca017207903504d0f
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858785B2

Reaction notes

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