Water → HCID 18965309, compound

HRID 2226758Notes

Reaction equation

HRID 2226758 reaction equation
[CH:1]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[CH2:10][CH2:11][CH2:12][C:5]=2[CH:4]=[CH:3][CH:2]=1.[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28]Cl.[NH2-].[Na+].O>C1(C)C=CC=CC=1>[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][N:7]1[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:12][CH2:11][CH2:10][C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 24533Sodium amideHCID 109657372-[2-(2-Chloroethoxy)ethoxy]oxaneHCID 12412218HCID 12412218, compound

Product 1

HCID 18965309HCID 18965309, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5,6,7,12-tetrahydrodibenz[b,g]azocine (2.5 g, 12 mmol, prepared in a similar way as described in Chem. Pharm. Bull. 1978, 26, 942-950) and 2-(2-((tetrahydro-2-pyranyl)oxy)ethoxy)ethylchloride (3.0 g, 14 mmol) in toluene (50 ml) was added a suspension of sodium amide (1.50 g, 19 mmol, 50% wt suspension in toluene). The reaction mixture was heated at reflux temperature for 10 h. The mixture was allowed to cool to room temperature and water (52.5 ml) was carefully added. The phases were separated and the aqueous phase was extracted with toluene (50 ml). The combined organic phases were washed with water (2×5 ml), brine (15 ml) and dried over magnesium sulphate. The solvent was evaporated in vacuo. The oily residue was submitted to column chromatography on silica gel (150 g) using a mixture of ethyl acetate and n-heptane (1:4) as eluent. Collecting the proper fractions afforded 3.0 g of crude 12-(2-(2 -((tetrahydro-2-pyranyl)oxy)ethoxy)ethyl)-5,6,7,12-tetrahydrodibenz[b,g]azocine. TLC: rf=0.11 (SiO2 ; ethyl acetate/n-heptane=1:4).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 10 h
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with toluene (50 ml)
  5. washThe combined organic phases were washed with water (2×5 ml), brine (15 ml)
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was evaporated in vacuo
  8. additiona mixture of ethyl acetate and n-heptane (1:4) as eluent
  9. customCollecting the proper fractions

Sources & evidence

ORD record
ord-4bc0b05cb9a04f86b9a0036417c0ccfc
Source dataset
uspto-grants-1994_09
Patent number
US05348965

Reaction notes

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