Acetonitrile → HCID 12398827, compound

HRID 329330Notes

Reaction equation

HRID 329330 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[C:14](Cl)=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2.C(#N)C.[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28][OH:29].C(N(CC)CC)C>O.CCOCC>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[C:14]([O:29][CH2:28][CH2:27][N:26]([CH3:30])[CH3:25])=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 79022-(Dimethylamino)ethanolHCID 8471TriethylamineHCID 203106912-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionyl chloride

Product 1

HCID 12398827HCID 12398827, compound

Reagents, catalysts & solvents 1

HCID 21584184Diethylether waterSolvent

Procedure

2-(5-Oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionyl chloride is dissolved in 25 ml. of acetonitrile with stirring, and treated with 1.0 ml. of dimethylethanolamine and 1.0 ml. of triethylamine. After the solution is stirred for 16 hours, it is added to a water/ether mixture, and the organic phase washed with water and then dried and evaporated to give a crude product which after chromatography on 10 g. silica gel, eluting with chloroform then chloroform: methanol (9:1), affords β-N,N,-dimethylaminoethyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate as an oil (hydrochloride salt: m.p. 136°-137° C; see Example XIV).

Workup

  1. additiontreated with 1.0 ml
  2. washthe organic phase washed with water
  3. customdried
  4. customevaporated
  5. customto give a crude product which after chromatography on 10 g
  6. washsilica gel, eluting with chloroform

Sources & evidence

ORD record
ord-adfe20571ec6466a92caa670bb8a1799
Source dataset
uspto-grants-1977_04
Patent number
US04020094

Reaction notes

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