Hydrochloric Acid → HCID 21553937, compound

HRID 267770Notes

Reaction equation

HRID 267770 reaction equation
O[C:2]1([CH2:13][NH:14][CH:15]=O)[CH2:8][O:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[ClH:25].Cl.OC1(CNC)COC2C=CC=CC=2OC1>C(O)C.O.CCOCC>[ClH:25].[CH3:15][NH:14][CH2:13][CH:2]1[CH2:8][O:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][CH2:3]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15557315HCID 15557315, compoundHCID 15557317HCID 15557317, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 21553937HCID 21553937, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

3-hydroxy-3-formamidomethyl-3,4-dihydro-2H-1,5-benzodioxepin (5.8 g.) in 200 ml. anhydrous ether is added to lithium aluminum hydride (2.0 g.) in 40 ml. of anhydrous ether dropwise in one hour. The mixture then is refluxed for 2 hours and the excess lithium aluminum hydride then decomposed with water (5.0 ml.) followed by 10% sodium hydroxide (3.6 ml.) followed by 6.0 ml. of water. The white solid formed is filtered and the filtrate dried over magnesium sulfate then over calcium sulfate. It is stripped affording 3.8 g. of oil. The oil is acidified with 11N hydrochloric acid in ethanol to give 3.7 g. of 3-hydroxy-3-methylaminomethyl-3,4-dihydro-2H-1,5-benzodioxepin hydrochloride, m.p. 189°-205°C. Following several recrystallizations from ethanol, the product melts at 217-219°C.

Workup

  1. temperatureThe mixture then is refluxed for 2 hours
  2. customThe white solid formed
  3. filtrationis filtered
  4. dry with materialthe filtrate dried over magnesium sulfate
  5. customIt is stripped affording 3.8 g
  6. customto give 3.7 g
  7. customrecrystallizations from ethanol

Sources & evidence

ORD record
ord-e5eef43931744db9ac6f6bea1598022d
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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