Triethylamine → HCID 53885292, compound

HRID 1637115Notes

Reaction equation

HRID 1637115 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:14]=1)[C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCN(CC)CC.[F:34][C:35]([F:42])([F:41])[C:36](OCC)=[O:37]>CO>[CH:22]1([O:21][C:15]2[CH:14]=[C:13]([CH:4]([C:5]#[C:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:3][NH:2][C:36](=[O:37])[C:35]([F:42])([F:41])[F:34])[CH:18]=[CH:17][C:16]=2[O:19][CH3:20])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 573652252-[3-(Cyclopentyloxy)-4-methoxyphenyl]-4-phenylbut-3-yn-1-amine--hydrogen chloride (1/1)

Product 1

HCID 53885292HCID 53885292, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (+/-)-4-amino-3-(3-cyclopentyloxy-4-methoxyphenyl)-1-phenyl-1-butyne hydrochloride (50 mg, 0.14 mmol) and Et3N (40 mg) in a mixture of MeOH (1 ml) and ethyl trifluoroacetate (0.5 ml) was refluxed overnight. The solvents were evaporated, the residue taken up in Et2O, washed with H2O, 0.01N HCl, dried, and the solvent evaporated. The residue was crystallized from a mixture of cyclohexane and Et2O, and gave the titled compound, 32 mg (55%). mp 143-145°. 1H NMR (400 MHz, CDCl3) δ 7.42 (m, 2 H), 7.32 (m, 3 H), 6.94 (m, 2 H), 6.84 (d, 1 H), 6.54 (broad s, 1 H), 4.78 (m, 1 H), 4.08 (t, 1 H), 3.82 (s, 3 H), 3.78 (m, 1 H), 3.58 (m, 1 H), 1.76-1.92 (m, 6 H), 1.60 (m, 2 H).

Workup

  1. temperaturewas refluxed overnight
  2. customThe solvents were evaporated
  3. washwashed with H2O, 0.01N HCl
  4. customdried
  5. customthe solvent evaporated
  6. customThe residue was crystallized from a mixture of cyclohexane and Et2O

Sources & evidence

ORD record
ord-eddb1cbff0b84f55b4dc47b529f5106e
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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