Triethylamine → HCID 14349041, compound

HRID 2107708Notes

Reaction equation

HRID 2107708 reaction equation
[O:1]([CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19](N(CC)CC)C.[Cl:26]C(OCC)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(Cl)(Cl)Cl.C1COCC1.CCOCC>[ClH:26].[CH3:19][N:10]1[CH2:9][CH:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 143490321-Phenoxy-2,3,4,5-tetrahydro-1H-3-benzazepineHCID 21226445Aluminium lithium hydride

Product 1

HCID 14349041HCID 14349041, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of 1-phenoxy-2,3,4,5-tetrahydro-3-benzazepine (3.9 g, 16 mmole) of Example 28b and triethylamine (1.8 g, 18 mmole) in chloroform (50 ml) was slowly added ethyl chloroformate (1.9 g, 18 mmole) in chloroform (10 ml). The reaction mixture was stirred two hours at ambient temperature, then was evaporated to an oil which was stirred with water and extracted with ether. The organic extracts were washed with dilute HCl, water, then dried (saturated NaCl, anhydrous MgSO4). The solution was filtered and concentrated to an oil (4.7 g, 93%). A solution of the oil in THF (40 ml) was slowly added to a cooled suspension of LiAlH4 (1.7 g, 45 mmol) in THF (100 ml). After stirring three hours at ambient temperature, the mixture was cooled, diluted with ether, then quenched by slow addition of saturated NH4Cl. The mixture was filtered, washed with water and dried (saturated NaCl, anhydrous MgSO4). The solution was filtered and concentrated to an oil which was converted by the addition of ethereal HCl to the hydrochloride salt (3 g 69%, d 211°-214° C.). This material was recrystallized from a 20:1 solution of ethyl acetate/methanol to yield 3-methyl-1-phenoxy-2,3,4,5-tetrahydro-3-benzazepine hydrochloride, d 224°-225° C.

Workup

  1. customwas evaporated to an oil which
  2. stirringwas stirred with water
  3. extractionextracted with ether
  4. washThe organic extracts were washed with dilute HCl, water
  5. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  6. filtrationThe solution was filtered
  7. concentrationconcentrated to an oil (4.7 g, 93%)
  8. stirringAfter stirring three hours at ambient temperature
  9. temperaturethe mixture was cooled
  10. customquenched by slow addition of saturated NH4Cl
  11. filtrationThe mixture was filtered
  12. washwashed with water
  13. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  14. filtrationThe solution was filtered
  15. concentrationconcentrated to an oil which
  16. additionwas converted by the addition of ethereal HCl to the hydrochloride salt (3 g 69%, d 211°-214° C.)
  17. customThis material was recrystallized from a 20:1 solution of ethyl acetate/methanol

Sources & evidence

ORD record
ord-b67edac71df24edbaee56d12e7adb81d
Source dataset
uspto-grants-1990_06
Patent number
US04935418

Reaction notes

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