Diisopropylethylamine → HCID 58437817, compound

HRID 2092389Notes

Reaction equation

HRID 2092389 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.Cl[CH2:12][CH2:13][N:14]([CH2:25][CH2:26]Cl)[S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16].CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:26][CH2:25][N:14]([S:15]([C:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)(=[O:17])=[O:16])[CH2:13][CH2:12]2)[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamideHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamine

Product 1

HCID 58437817HCID 58437817, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of (S)-1-(4-bromophenyl)ethanamine (0.36 ml, 2.50 mmol) and N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide (864 mg, 2.62 mmol) in DIPEA (0.873 ml, 5.0 mmol) was heated at 125° C. and stirred for 20 h. The reaction mixture was cooled to RT then diluted into DCM (30 ml) and washed with Na2CO3 2M in water (40 ml). The aqueous phase was further extracted with DCM (3×20 ml) and the combined organic fractions were dried over Na2SO4, filtered and evaporated to dryness. AcOEt was added in small portions into a hot mixture of the crude in heptane until complete dissolution. The mixture was allowed to cooled to RT during which time precipitation occurred. The mixture was cooled to 0° C. (ice bath) for 30 min then filtered. The solid was washed with heptane, dried under air and finally under high vacuum to yield the title compound (810 mg, 1.91 mmol, 77% yield) as a brownish solid. HPLC: AtRet=1.66 min; LC-MS: m/z 425.4 [M+H]+; 1H NMR (400 MHz, CDCl3): 1.29 (d, J=6.8, 3H), 2.41-2.50 (m, 5H), 2.52-2.61 (m, 2H), 2.93-3.05 (m, 4H), 3.34 (q, J=6.7, 1H), 7.09-7.16 (m, 2H), 7.31-7.37 (m, 2H), 7.39-7.44 (m, 2H), 7.61-7.66 (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with Na2CO3 2M in water (40 ml)
  3. extractionThe aqueous phase was further extracted with DCM (3×20 ml)
  4. dry with materialthe combined organic fractions were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. additionAcOEt was added in small portions into a hot mixture of the crude in heptane until complete dissolution
  8. temperatureto cooled to RT during which time precipitation
  9. temperatureThe mixture was cooled to 0° C. (ice bath) for 30 min
  10. filtrationthen filtered
  11. washThe solid was washed with heptane
  12. customdried under air and finally under high vacuum

Sources & evidence

ORD record
ord-c12d4c4bf2324fedbb8607ae55ca6529
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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