Dimethylamine → HCID 178419213, compound

HRID 279970Notes

Reaction equation

HRID 279970 reaction equation
[NH:1]([CH3:3])[CH3:2].CN(C)C.[CH2:8]([NH:10][C:11]([BH2:13])=[O:12])[CH3:9].CCCCC>C(Cl)Cl>[CH3:2][NH:1][CH3:3].[CH2:8]([NH:10][C:11]([BH2:13])=[O:12])[CH3:9]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8003PentaneHCID 178419214HCID 178419214, compound

Product 1

HCID 178419213HCID 178419213, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Anhydrous (CH3)2NH (50 g, 1.1 mol) was cooled to 0° C. and poured into the glass pressure vessel containing 1 (14.38 g, 0.1 mol) kept at 0° C. The vessel was assembled and kept at room temperature for 81/2 days with occasional shaking each day. The reaction vessel was then cooled to 0° C. and slowly opened. To this solution was added ca. 8 mL of pentane, and the volatile amines were allowed to evaporate off. The remaining amines and solvent were removed by rotary evaporation. A pale yellow liquid was obtained that had ca. 21% unreacted 1 (by proton NMR). The mixture was taken up in CH2Cl2 and washed once with water. The water washing was repeatedly extracted with CH2Cl2 and the proton NMR spectrum of the CH2Cl2 showed that it contained only the starting amide (1). The CH2Cl2 solution containing the product, uncontaminated by 1 (by proton NMR), was dried over MgSO4 and treated with charcoal. The solvent was then removed by rotary evaportation (and the pale yellow oil (10.1 g (77.7%)) was vacuum distilled: bp 110°-112° C. (0.2 torr); IR (CH2Cl2) 3440 (ν(NH)), 2965 (ν(CH)), 2365 (ν(BH)), 1590 (amide I), 1490 (amide II) cm-1, 1HNMR(CDCl3) δ 1.06 (t, CH3CH2), 2.40 (d, CH3N), 3.18 (m, CH2CH3), 5.80 (br s, amine H), 6.45 (br s, amide H); 11BNMR (CDCl3, BF3Et2O)-11.55 (t, JB-H =88 HZ); 13C NMR (CDCl3) 15.26 (CH3CH2, 32.33 (CH2CH3), 42.91 (CH3N). Anal. Calcd for C3H15BN2O: C, 46.20; H, 11.63; N 21.55. Found: C, 45.94; H, 11.58; N, 21.30.

Workup

  1. additionpoured into the glass pressure vessel
  2. customkept at 0° C
  3. customkept at room temperature for 81
  4. custom2 days
  5. customto evaporate off
  6. customThe remaining amines and solvent were removed by rotary evaporation
  7. customA pale yellow liquid was obtained
  8. washwashed once with water
  9. extractionThe water washing was repeatedly extracted with CH2Cl2
  10. additionThe CH2Cl2 solution containing the product
  11. dry with materialuncontaminated by 1 (by proton NMR), was dried over MgSO4
  12. additiontreated with charcoal
  13. customThe solvent was then removed by rotary evaportation (and the pale yellow oil (10.1 g (77.7%))
  14. distillationdistilled

Sources & evidence

ORD record
ord-68b4c2d3999d488f8a6092df139919ec
Source dataset
uspto-grants-1986_05
Patent number
US04587359

Reaction notes

Loading…