Triethylamine → HCID 10436687, compound

HRID 1684508Notes

Reaction equation

HRID 1684508 reaction equation
[CH3:1][C:2]([CH3:8])([CH2:6][CH3:7])[C:3](Cl)=[O:4].[CH2:9]([NH:11][CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]([N:24]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[C:28](=[O:35])[NH:27][C:26]3[CH:36]=[CH:37][CH:38]=[N:39][C:25]2=3)=[O:23])[CH2:17][CH2:16]1)[CH3:10].C(N(CC)CC)C>O1CCCC1>[CH3:1][C:2]([CH3:8])([CH2:6][CH3:7])[C:3]([N:11]([CH2:9][CH3:10])[CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]([N:24]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[C:28](=[O:35])[NH:27][C:26]3[CH:36]=[CH:37][CH:38]=[N:39][C:25]2=3)=[O:23])[CH2:17][CH2:16]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 799582,2-Dimethylbutyryl chlorideHCID 190394125,11-dihydro-11-[[4-[3-(ethylamino)propyl]-1-piperidinyl]acetyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 10436687HCID 10436687, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

1.48 g (0.01 mol) of 2,2-dimethylbutyric acid chloride dissolved in 20 ml of tetrahydrofuran are added dropwise, with stirring, at ambient temperature, to a solution of 4.2 g (0.01 mol) of 5,11-dihydro-11-[[4-[3-(ethylamino)propyl]-1-piperidinyl]acetyl]-6H-pyrido-[2,3-b][1,4]benzodiazepin-6-one and 2 ml of triethylamine in 150 ml of tetrahydrofuran. In order to complete the reaction the solution is stirred for a further hour at 50° C. After cooling, the precipitated triethylamine hydrochloride is filtered off and the filtrate is evaporated to dryness using a rotary evaporator in a water jet vacuum. In order to purify it the residue is dissolved in ethyl acetate. The ethyl acetate solution is extracted twice with 10% hydrochloric acid, the organic phase is separated off and the aqueous phase is made alkaline by the addition of concentrated ammonia. Then the aqueous phase is extracted twice with ethyl acetate. The organic phase is dried over sodium sulphate and evaporated to dryness in vacuo. The residue obtained is crystallised by digesting it in ethyl acetate. Colourless crystals are obtained of m.p. 136°-138° C.

Workup

  1. additionare added dropwise
  2. customthe reaction the solution
  3. temperatureAfter cooling
  4. filtrationthe precipitated triethylamine hydrochloride is filtered off
  5. customthe filtrate is evaporated to dryness
  6. customa rotary evaporator in a water jet vacuum
  7. customIn order to purify it the residue
  8. dissolutionis dissolved in ethyl acetate
  9. extractionThe ethyl acetate solution is extracted twice with 10% hydrochloric acid
  10. customthe organic phase is separated off
  11. additionby the addition of concentrated ammonia
  12. extractionThen the aqueous phase is extracted twice with ethyl acetate
  13. dry with materialThe organic phase is dried over sodium sulphate
  14. customevaporated to dryness in vacuo
  15. customThe residue obtained
  16. customis crystallised
  17. customColourless crystals are obtained of m.p. 136°-138° C.

Sources & evidence

ORD record
ord-e068d30841194bdf8118f7a9eb9c4dd9
Source dataset
uspto-grants-1997_06
Patent number
US05641772

Reaction notes

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