Triethylamine → HCID 14349053, compound

HRID 704671Notes

Reaction equation

HRID 704671 reaction equation
[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][C:6]2[CH:7]([O:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.C(N(CC)CC)C.Cl[C:35]([O:37][CH2:38][CH3:39])=[O:36]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][C:6]2[CH:7]([O:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][CH:14]=3)[CH2:8][N:9]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14349051HCID 14349051, compound

Product 1

HCID 14349053HCID 14349053, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a cooled solution of 7,8-dimethoxy-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine (5.5 g, 0.015 mole) and triethylamine (1.7 g, 0.017 mole) in chloroform (70 ml) was slowly dropped a solution of ethyl chloroformate (1.0 g, 0.017 mole) in chloroform (20 ml). After stirring twenty hours at ambient temperatures the reaction mixture was concentrated to an oil which was dissolved in ether, washed with water, dilute HCl, again twice with water, then dried (saturated NaCl, anhydrous MgSO4). The solution was filtered then concentrated to a solid (5.0 g, 76%, m.p. 120° C.) of which a sample was twice recrystallized from hexanes to yield 7,8-dimethoxy-3-ethoxycarbonyl-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine, m.p. 130°-131° C.

Workup

  1. concentrationwas concentrated to an oil which
  2. dissolutionwas dissolved in ether
  3. washwashed with water, dilute HCl, again twice with water
  4. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  5. filtrationThe solution was filtered
  6. concentrationthen concentrated to a solid (5.0 g, 76%, m.p. 120° C.) of which a sample
  7. customwas twice recrystallized from hexanes

Sources & evidence

ORD record
ord-a567d18a58544ed8bca303ef2f0bfd2c
Source dataset
uspto-grants-1991_01
Patent number
US04988690

Reaction notes

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