Triethylamine → HCID 13607655, compound

HRID 651994Notes

Reaction equation

HRID 651994 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:35]=[CH:34][C:24]4[C:25]([C:31](O)=[O:32])=[C:26]([CH3:30])[C:27](=[O:29])[O:28][C:23]=4[CH:22]=3)[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>O.O1CCCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:35]=[CH:34][C:24]4[C:25]([CH2:31][OH:32])=[C:26]([CH3:30])[C:27](=[O:29])[O:28][C:23]=4[CH:22]=3)[CH2:15][CH2:16]2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 88670696HCID 88670696, compound

Product 1

HCID 13607655HCID 13607655, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1.7 g. (3 mmol) 7-{3-{4-[(4-chlorophenyl)-methyl]-1-piperazinyl}-propoxy}-3-methyl-2H-1-benzopyran-2-one-4-carboxylic acid dihydrochloride, 0.98 g. (8.7 mmol) anhydrous triethylamine and 20 ml. anhydrous tetrahydrofuran is stirred for 30 minutes at ambient temperature. The reaction mixture is then cooled and a solution of 0.38 g. (3.5 mmol) ethyl chloroformate and 10 ml. anhydrous tetrahydrofuran added dropwise thereto at an internal temperature of from -5° to -10° C. The reaction mixture is allowed to react for 30 minutes at -5° C. and subsequently the precipitated triethylamine hydrochloride is filtered off with suction with the exclusion of moisture. The filtrate is added dropwise at +10° C. to a suspension of 93 mg. (2.5 mmol) sodium borohydride and 1.5 ml. water. The reaction mixture is now stirred for 2 hours at ambient temperature, subsequently evaporated in a vacuum and the residue mixed with a mixture of ice and sodium hydrogen carbonate solution. It is then extracted several times with ethyl acetate and the extract is dried with anhydrous sodium sulphate and finally evaporated. After recrystallisation from ethanol, there is obtained 0.84 g. (59% of theory) of base; m.p. 135° C.; dihydrochloride m.p. 241° C., after recrystallisation from methanol.

Workup

  1. additionA mixture of 1.7 g
  2. temperatureThe reaction mixture is then cooled
  3. customof from -5° to -10° C
  4. customto react for 30 minutes at -5° C.
  5. filtrationsubsequently the precipitated triethylamine hydrochloride is filtered off with suction with the exclusion of moisture
  6. additionThe filtrate is added dropwise at +10° C. to a suspension of 93 mg
  7. customsubsequently evaporated in a vacuum
  8. additionthe residue mixed with a mixture of ice and sodium hydrogen carbonate solution
  9. extractionIt is then extracted several times with ethyl acetate
  10. dry with materialthe extract is dried with anhydrous sodium sulphate
  11. customfinally evaporated
  12. customAfter recrystallisation from ethanol
  13. customthere is obtained 0.84 g
  14. customdihydrochloride m.p. 241° C., after recrystallisation from methanol

Sources & evidence

ORD record
ord-1da43d79dc334bcdace3ed4ca089c23c
Source dataset
uspto-grants-1987_06
Patent number
US04670439

Reaction notes

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