Triethylamine → HCID 68128176, compound

HRID 1077045Notes

Reaction equation

HRID 1077045 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.C(N(CC)CC)C.C(Cl)(=[O:33])C(C)C>ClCCl>[CH:8]([C:9]([CH:14]([CH3:15])[CH3:13])=[O:33])([CH3:17])[CH3:7].[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

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 67838308HCID 67838308, compound

Product 1

HCID 68128176HCID 68128176, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.5 g. of the product of Example 1 in 150 ml. of dichloromethane containing 25 ml. of triethylamine a solution of 4.2 ml. of isobutyryl chloride in approximately 25 ml. of dichloromethane is added dropwise, with constant stirring. On heating to reflux, the white precipitate originally formed redissolves. Refluxing is continued for 2 hours; the solution is cooled, washed with water and with saturated sodium bicarbonate, dried over anhydrous potassium carbonate, and stripped down to a dark gum, which is taken up in hexane, boiled and decolorized. After concentrating the clear solution tp 100 ml. and cooling, a gum separates which solidifies completely on standing. After 1 week, 1,2,3,4,8,9-hexahydropyrido[4', 3':2,3]indolo[1,7-ab][1]benzazepin isopropyl ketone, m.p. 122°-124°, is isolated.

Workup

  1. temperatureOn heating
  2. temperatureto reflux
  3. customthe white precipitate originally formed
  4. dissolutionredissolves
  5. temperatureRefluxing
  6. temperaturethe solution is cooled
  7. washwashed with water and with saturated sodium bicarbonate
  8. dry with materialdried over anhydrous potassium carbonate
  9. concentrationAfter concentrating the clear solution tp 100 ml
  10. temperatureand cooling
  11. waitAfter 1 week

Sources & evidence

ORD record
ord-680c4511925145ba88b8d615c3dd5784
Source dataset
uspto-grants-1976_05
Patent number
US03959300

Reaction notes

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