Cyclopropylamine → HCID 57546092, compound

HRID 913881Notes

Reaction equation

HRID 913881 reaction equation
[N:1]([C:4]1[C:11]([Br:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:5]=1[CH:6]=O)=[N+:2]=[N-].[CH:14]1(N)[CH2:16][CH2:15]1>C(Cl)Cl>[Br:12][C:11]1[C:4]2[C:5](=[CH:6][N:2]([CH:14]3[CH2:16][CH2:15]3)[N:1]=2)[CH:8]=[C:9]([Cl:13])[CH:10]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 57546000HCID 57546000, compound

Product 1

HCID 57546092HCID 57546092, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Azido-3-bromo-5-chlorobenzaldehyde (1.38 g, 5.30 mmol) and cyclopropylamine (0.37 mL, 5.30 mmol) in methylene chloride (20 mL) were treated with molecular sieves (1.5 g). The reaction was stirred at room temperature for 2 h, filtered over celite and the resulting solution evaporated in vacuo. The resulting oil was suspended in toluene (15 mL) and heated at reflux for 2 h. After cooling to room temperature, the mixture was poured into ice water and extracted with diethyl ether (2×). The organic layers were pooled together, washed with brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (15% ethyl acetate/hexanes) gave 1.1 g (76%) as a light yellow solid. 1H-NMR (CDCl3, 500 MHz) δ 8.7 (s, 1H), 7.81 (d, J=2.6 Hz, 1H), 7.53 (d, J=2.6 Hz, 1H), 3.05-3.09 (m, 1H), 0.95-0.99 (m, 4H). Mass spec.: 273.03 (MH)+.

Workup

  1. filtrationfiltered over celite
  2. customthe resulting solution evaporated in vacuo
  3. temperatureheated
  4. temperatureat reflux for 2 h
  5. temperatureAfter cooling to room temperature
  6. additionthe mixture was poured into ice water
  7. extractionextracted with diethyl ether (2×)
  8. washwashed with brine (2×)
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customColumn chromatography on silica gel (15% ethyl acetate/hexanes) gave 1.1 g (76%) as a light yellow solid

Sources & evidence

ORD record
ord-05998c2dba1b46b5a2d855f6be0b80cf
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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