Dimethylcarbamoyl Chloride → HCID 131718494, compound

HRID 1109224Notes

Reaction equation

HRID 1109224 reaction equation
[OH:1][C:2]1[C:14]2[CH2:13][CH2:12][C@H:11]3[C@H:7]([CH2:8][CH2:9][N:10]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:25](=[O:26])[CH2:24][C:23]([CH3:28])([CH3:27])[CH2:22][C:21]3=[O:29])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:37][N:38]([CH3:42])[C:39]([Cl:41])=[O:40]>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[ClH:41].[CH3:37][N:38]([CH3:42])[C:39](=[O:40])[O:1][C:2]1[C:14]2[CH2:13][CH2:12][C@H:11]3[C@H:7]([CH2:8][CH2:9][N:10]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:21](=[O:29])[CH2:22][C:23]([CH3:27])([CH3:28])[CH2:24][C:25]3=[O:26])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 131718492HCID 131718492, compound

Product 1

HCID 131718494HCID 131718494, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

5.0 g (12.54 mmol) of rac-cis-1-[5-(6-hydroxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)pentyl]-4,4-dimethylpiperidine-2,6-dione were dissolved in 250 ml of toluene, treated with 2.67 g (3.7 ml; 26.4 mmol) of triethylamine, 1.62 g (1.4 ml, 15.4 mmol) of dimethylcarbamoyl chloride and 250 mg of 4-dimethylaminopyridine and stirred overnight in an oil bath at an oil bath temperature of 110°. After cooling the organic phase was washed in succession with water, sodium bicarbonate solution and water, dried over magnesium sulphate and evaporated. The brown oil obtained (6.3 g) was chromatographed over a 30-fold amount of silica gel with methylene chloride/ethyl acetate 1:1 and the purified base (5.9 g of pale yellow oil) was converted into the hydrochloride in the usual manner. After crystallization from ethyl acetate/ether there were obtained 5.1 g (80%) of rac-cis-3-[5-(4,4-dimethyl-2,6-dioxopiperidin-1-yl)pentyl]-2,3,3a, 4,5,9b-hexahydro-1H-benzo[e]indol-6-yl dimethylcarbamate hydrochloride in the form of yellowish crystals of m.p. 133°-135° (dec.).

Workup

  1. temperatureAfter cooling the organic phase
  2. washwas washed in succession with water, sodium bicarbonate solution and water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe brown oil obtained (6.3 g)
  6. customwas chromatographed over a 30-fold amount of silica gel with methylene chloride/ethyl acetate 1:1
  7. customAfter crystallization from ethyl acetate/ether there

Sources & evidence

ORD record
ord-d67fa2cff1a94cbc9b90ec3bc179378d
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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