Water → HCID 20491803, compound

HRID 434707Notes

Reaction equation

HRID 434707 reaction equation
[NH2:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[CH2:13])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH2:3]1.[OH-].[Na+].O.[C:21](=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[N+:1]([CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[CH2:13])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH2:3]1)#[C-:21]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide3×HCID 10536971HCID 10536971, compound

Product 1

HCID 20491803HCID 20491803, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalyst2×HCID 6212ChloroformSolvent

Procedure

To a solution of 10-amino-5-methylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (8.1 g, 36.6 mmole) in chloroform (180 ml) was added sodium hydroxide pellets (4.42 g, 0.11 mole) benzyltriethylammonium chloride (0.42 g, 1.8 mmole) and water (0.5 ml). The mixture was stirred under nitrogen until the sodium hydroxide pellets dissolved (ca 4 hours), treated with anhydrous potassium carbonate, filtered, and evaporated to dryness in vacuo. The resulting oil was dissolved in chloroform (180 ml), treated with another 1.5 g (37.5 mmole) of sodium hydroxide and 0.2 g (0.86 mmole) of benzyltriethylammonium chloride, and stirred overnight under nitrogen. The mixture was again dried over potassium carbonate, filtered, and evaporated to dryness in vacuo. The resulting oil was chromatographed on 120 g of silica gel, and eluted with methylene chloride. The combined product fractions were evaporated to dryness in vacuo and the resulting solid was recrystallized from ether to give 4 g of solid, m.p. 96°-98°.

Workup

  1. dissolutionpellets dissolved (ca 4 hours)
  2. filtrationfiltered
  3. customevaporated to dryness in vacuo
  4. dissolutionThe resulting oil was dissolved in chloroform (180 ml)
  5. dry with materialThe mixture was again dried over potassium carbonate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customThe resulting oil was chromatographed on 120 g of silica gel
  9. washeluted with methylene chloride
  10. customThe combined product fractions were evaporated to dryness in vacuo
  11. customthe resulting solid was recrystallized from ether

Sources & evidence

ORD record
ord-8edfb5ecc51c4331aed9aa5532f03a31
Source dataset
uspto-grants-1983_08
Patent number
US04399141

Reaction notes

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