Propionyl chloride → HCID 23449356, compound

HRID 479838Notes

Reaction equation

HRID 479838 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH:12]2[C:10]([CH2:15][NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:32](Cl)(=[O:35])[CH2:33][CH3:34]>C(Cl)Cl>[CH2:1]([N:8]1[CH2:14][CH2:13][CH:12]2[C:10]([CH2:15][N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:32](=[O:35])[CH2:33][CH3:34])([CH2:11]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 21904394HCID 21904394, compound

Product 1

HCID 23449356HCID 23449356, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the a solution of 3-Benzyl-3-aza-bicyclo[4.1.0]hept-1-ylmethyl)-phenyl-amine (175) (250 mg, 0.86 mmol) in CH2Cl2 (2 ml) at 0° C. was added i-Pr2NEt (0.30 ml, 1.72 mmol)) and propionyl chloride (0.11 ml, 1.29 mmol). The mixture was stirred for 2 hrs. The mixture was diluted with CH2Cl2 (5 ml), washed with sat. NaHCO3 (2×5 ml), brine (5 ml) and water (5 ml) and dried with Na2SO4. After filtration, the filtrate was concentrated under vacuum. The residue was purified by silica gel chromatography (0.5% to 2% MeOH in CH2Cl2) to give 176 as a colorless oil. 1H-NMR (300 MHz, CDCl3) δ 7.41-7.20 (m, 10H), 4.20 (d, 1H), 3.42 (AB, 2H), 3.21 (d, 1H), 2.65 (q, 2H), 2.20-2.00 (m, 4H), 1.80-1.60 (m, 2H), 1.30 (m, 1H), 1.05 (t, 3H), 0.80-0.20 (m, 2H) ppm; LRMS (calculated for C23H28N2O) 348, found 348; IR (film) 3308, 3105, 3064, 2978, 2937, 2874, 2811, 1689m 1666, 1598, 1540, 1499, 1445, 1314, 1246, 1196, 1074, 757 cm−1.

Workup

  1. washwashed with sat. NaHCO3 (2×5 ml), brine (5 ml) and water (5 ml)
  2. dry with materialdried with Na2SO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe residue was purified by silica gel chromatography (0.5% to 2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-7f04f4cff90d42019d3e0d0d1be2822a
Source dataset
uspto-grants-2003_11
Patent number
US06645980B1

Reaction notes

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