Triethylamine → HCID 15860308, compound

HRID 1291708Notes

Reaction equation

HRID 1291708 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C@@H:10]1[CH2:12][C@H:11]1[CH2:13][NH2:14].CCN(CC)CC.[C:22](Cl)(=[O:26])[CH:23]([CH3:25])[CH3:24]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C@@H:10]1[CH2:12][C@H:11]1[CH2:13][NH:14][C:22](=[O:26])[CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 53965268HCID 53965268, compound

Product 1

HCID 15860308HCID 15860308, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of (trans)-2-(2-fluoro-5-methoxyphenyl)cyclopropanemethanamine (600 mg, 3.1 mmol), Et3N (909 mg, 9.0 mmol), in dry dichloromethane (15 mL) at 0° C. was added isobutyryl chloride (352 mg, 3.3 mmol) dropwise. The resulting suspension was then allowed to warm to room temperature and stirred for 18 h. The solvents were removed and the residue was taken into EtOAc (100 mL) and washed sequentially with H2O, 5% citric acid, 5% K2CO3, brine, and dried over K2CO3. Concentration by rotary evaporation yielded a crude oil which was then purified by Kugelrohr distillation. Recrystallization of the resultant solid from Et2O/hexane (1:1) gave 380 mg (47% yield) of the title compound: mp 93°-94° C.; 1H NMR (300 MHz, CDCl3) δ0.82-0.88 (m, 1H), 0.97-1.03 (m, 1H), 1.13 (d, J=8.1 Hz, 6H), 1.14-1.24 (m, 1H), 1.85-1.91 (m, 1H), 2.25-2.30 (m, 1H), 2.93-3.02 (m, 1H), 3.52 (dt, I=7.8, 13.8 Hz, 1H), 3.72 (s, 3H), 5.74 (br s, 1H), 6.41-6.44 (m, 1H), 6.59-6.64 (m, 1H), 6.91 (t, J=6.5 Hz, 1H); IR (NaCl Film) 3298, 2962, 1642, 1546, 1502, 1428 cm-1 ; MS (isobutane--DCI) m/e 253; Analysis calc'd for C15H20NO2F: C, 67.90; H, 7.60; N, 5.28; found: C, 68.18; H, 7.77; N, 5.24.

Workup

  1. customThe solvents were removed
  2. washwashed sequentially with H2O, 5% citric acid, 5% K2CO3, brine
  3. dry with materialdried over K2CO3
  4. concentrationConcentration
  5. customby rotary evaporation
  6. customyielded a crude oil which
  7. distillationwas then purified by Kugelrohr distillation
  8. customRecrystallization of the resultant solid from Et2O/hexane (1:1)

Sources & evidence

ORD record
ord-0679823a8b87494388596541336ff2fe
Source dataset
uspto-grants-1998_05
Patent number
US05753709

Reaction notes

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