Dichloromethane → HCID 70633015, compound

HRID 1077047Notes

Reaction equation

HRID 1077047 reaction equation
[CH2:1]1[C:11]2[N:10]3[C:12]4[CH:21]=[CH:20][N:19]=[CH:18][C:13]=4[C:14]4[CH2:15][CH2:16][CH:17]=[C:8]([C:9]=43)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3][CH2:2]1.ClCCl.[CH:25]1([C:28](Cl)=[O:29])[CH2:27][CH2:26]1>C(N(CC)CC)C>[CH2:1]1[C:11]2[N:10]3[C:12]4[CH:21]=[CH:20][N:19]=[CH:18][C:13]=4[C:14]4[CH2:15][CH2:16][CH:17]=[C:8]([C:9]=43)[CH:7]=[CH:6][C:5]=2[CH2:4][CH:3]([C:28]([CH:25]2[CH2:27][CH2:26]2)=[O:29])[CH2:2]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 77637Cyclopropanecarbonyl chlorideHCID 67838308HCID 67838308, compound

Product 1

HCID 70633015HCID 70633015, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 16.4 g. of the product of Example 1 in 500 ml. of dichloromethane, 7.3 g. of cyclopropanecarbonyl chloride is added, followed by dropwise addition of 10 ml. of triethylamine. A mildly exothermic reaction takes place, after which stirring of the mixture is continued at room temperature overnight. The mixture is then washed with 1N hydrochloric acid and water, and dried over anhydrous sodium carbonate. On evaporation to dryness, crude cyclopropyl 1,2,3,4,8,9-hexahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepin-3-yl ketone is obtained as a glassy product, m.p. 149°-152° on recrystallization from ethanol. A solution of 8.6 g. of this material in 120 ml. of tetrahydrofuran is added dropwise to a suspension of 2.3 g. of lithium aluminum hydride in 180 ml. of tetrahydrofuran. On completion of the addition, the mixture is first refluxed for 4 hours, then allowed to stir at room temperature overnight and finally decomposed in the usual manner. After filtering off the inorganic salts, the filtrate is dried over anhydrous sodium carbonate, evaporated in vacuo; the residue is dissolved in a 1:1 mixture of ethyl acetate-benzene and chromatographed on a 14 × 2.2 cm. column of basic alumina, activity I. The eluate is taken down to dryness; the residual oil dissolved in absolute alcohol, saturated with ethanolic hydrogen chloride, and once again evaporated to dryness. Upon crystallization of the residue from acetone, 3-(cyclopropylmethyl)-1,2,3,4,8,9-hexahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine hydrochloride, m.p. 267°, is obtained.

Workup

  1. additionfollowed by dropwise addition of 10 ml
  2. customA mildly exothermic reaction
  3. washThe mixture is then washed with 1N hydrochloric acid and water
  4. dry with materialdried over anhydrous sodium carbonate
  5. customOn evaporation to dryness

Sources & evidence

ORD record
ord-7de23b1e15034971a2071b0801bcc28b
Source dataset
uspto-grants-1976_05
Patent number
US03959300

Reaction notes

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