Hydrogen iodide → HCID 67320762, compound

HRID 1894782Notes

Reaction equation

HRID 1894782 reaction equation
C[O:2][C:3]1[CH:22]=[CH:21][C:6]2[O:7][CH2:8][C:9]3[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=3[CH:11]([CH2:12][CH2:13][CH2:14][NH:15][CH3:16])[C:5]=2[CH:4]=1.I>C(O)(=O)C>[OH:2][C:3]1[CH:22]=[CH:21][C:6]2[O:7][CH2:8][C:9]3[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=3/[C:11](=[CH:12]/[CH2:13][CH2:14][NH:15][CH3:16])/[C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 67320099HCID 67320099, compound

Product 1

HCID 67320762HCID 67320762, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-methoxy-11-(3-methylaminopropyl)-6,11-dihydrodibenzo[b,e]oxepin (0.005 mol) with glacial acetic acid (0.2 ml) and hydriodic acid (0.2 ml, 57%) is stirred and heated for 5 hr at 90° C. The product is then extracted and purified by pouring into ice water (25 mL), made alkaline with sodium hydroxide (2N) and extracted with ether (2×10 mL). The aqueous layer is then adjusted to pH 6.8 with hydrochloric acid (6N). The mixture is then brought to pH 7 by the addition of sodium bicarbonate solution (5%) and extracted with chloroform (2×10 mL). The extract is dried over anhydrous sodium sulfate and evaporated in vacuo to give a yellowish solid. The crude reaction product is purified by preparative TLC (chloroform/toluene/methanol/ammonia, 4:3:2:1, v/v).

Workup

  1. extractionThe product is then extracted
  2. custompurified
  3. additionby pouring into ice water (25 mL)
  4. extractionextracted with ether (2×10 mL)
  5. additionThe mixture is then brought to pH 7 by the addition of sodium bicarbonate solution (5%)
  6. extractionextracted with chloroform (2×10 mL)
  7. dry with materialThe extract is dried over anhydrous sodium sulfate
  8. customevaporated in vacuo
  9. customto give a yellowish solid
  10. customThe crude reaction product
  11. customis purified by preparative TLC (chloroform/toluene/methanol/ammonia, 4:3:2:1

Sources & evidence

ORD record
ord-26f8a7a41fd348f89a9ee08d3e16b0aa
Source dataset
uspto-grants-2013_08
Patent number
US08513299B2

Reaction notes

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