Dichloromethane → HCID 86733945, compound

HRID 1576261Notes

Reaction equation

HRID 1576261 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][C:8]3([C:23]4[CH:22]=[CH:21][CH:20]=[C:19]([O:24]C)[C:18]=4[CH2:17][C:16]4[C:11]3=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.C(Cl)[Cl:27]>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[ClH:27].[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][C:8]3([C:23]4[CH:22]=[CH:21][CH:20]=[C:19]([OH:24])[C:18]=4[CH2:17][C:16]4[C:11]3=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH2:7][CH2:6]2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 86733947HCID 86733947, compound

Product 1

HCID 86733945HCID 86733945, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
0 °C

Procedure

Borontribromide (2 ml.) in methylene chloride (20 ml.) is added with stirring at 0°C. to a mixture of 1'-cyclopropylmethyl-4-methoxy,9,10-dihydroanthracene-9-spiro-4'-piperidine (1.8 g.) and sodium bicarbonate (5 g.). The reaction mixture is stirred at 0°C. for 2 hours and then at room temperature for 1 hour and diluted with chloroform, more sodium bicarbonate is added, the supension is washed thoroughly with water, dried (MgSO4) and evaporated. The residue is dissolved in boiling methanol, saturated ethereal hydrogen chloride is added, and the precipitated hydrochloride is collected and recrystallised twice from methanol-ether to give 1'-cyclopropylmethyl-4-hydroxy-9,10-dihydroanthracene-9-spiro-4'-piperidine hydrochloride m.p. 290°C. (decomposition).

Workup

  1. waitat room temperature for 1 hour
  2. additionis added
  3. washthe supension is washed thoroughly with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. dissolutionThe residue is dissolved
  7. additionis added
  8. customthe precipitated hydrochloride is collected
  9. customrecrystallised twice from methanol-ether

Sources & evidence

ORD record
ord-8505bd0f9178497aafc5350c9ea42faf
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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