Triethylamine → HCID 14349021, compound

HRID 346061Notes

Reaction equation

HRID 346061 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:20]=[CH:19][C:6]([O:7][CH:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:5][CH:4]=1.[CH2:23]([N:25](CC)CC)[CH3:24].Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32]>C(Cl)(Cl)Cl>[CH2:34]([O:33][C:31]([NH:25][CH2:23][CH2:24][N:10]1[CH2:9][CH:8]([O:7][C:6]2[CH:19]=[CH:20][C:3]([C:2]([F:1])([F:21])[F:22])=[CH:4][CH:5]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11]1)=[O:32])[CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 143489861-[4-(Trifluoromethyl)phenoxy]-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 14349021HCID 14349021, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a cooled solution of 3-aminoethyl)-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine of Example 21b (5.5 g, 0.016 mole) and triethylamine (1.8 g, 0.018 mole) in chloroform (75 ml) was slowly dropped a solution of ethyl chloroformate (2.0 g, 0.018 mole) in chloroform (25 ml). After stirring twenty hours at ambient temperature the reaction mixture was concentrated to a semisolid which was dissolved in ether, washed with water and dried (saturated NaCl, anhydrous MgSO4). The solution was filtered and concentrated to yield an oil. A sample of the resultant oil was distilled to yield an oil of 3-(2-ethoxycarbonylaminoethyl)-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine, bp 235°-238° C./0.10 mm.

Workup

  1. concentrationwas concentrated to a semisolid which
  2. dissolutionwas dissolved in ether
  3. washwashed with water
  4. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. customto yield an oil
  8. distillationA sample of the resultant oil was distilled

Sources & evidence

ORD record
ord-c72b842621d14b1aac90c2064d0b9a55
Source dataset
uspto-grants-1991_10
Patent number
US05059688

Reaction notes

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