Hexane → HCID 71495426, compound

HRID 588060Notes

Reaction equation

HRID 588060 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:22]=[CH:21][CH:20]=[CH:19][C:16]=2[CH2:17]Cl)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:30][C:31]1[CH:45]=[CH:44][C:34]([CH2:35][N:36]2[CH2:41][CH2:40][O:39][CH:38]([CH2:42][NH2:43])[CH2:37]2)=[CH:33][CH:32]=1.CCCCCC.CC(=O)[O:54]CC>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:22]=[CH:21][CH:20]=[CH:19][C:16]=2[C:17]([NH:43][CH2:42][CH:38]2[O:39][CH2:40][CH2:41][N:36]([CH2:35][C:34]3[CH:44]=[CH:45][C:31]([F:30])=[CH:32][CH:33]=3)[CH2:37]2)=[O:54])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 8058HexaneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 102427352-Aminomethyl-4-(4-fluorobenzyl)morpholineHCID 90386549HCID 90386549, compound

Product 1

HCID 71495426HCID 71495426, compoundYield 53%

Procedure

The solution obtained in step 1 was cooled to 4-5° C. in an ice bath, followed by dropwise adding triethylamine (0.42 ml, 3.0 mmol) for 5 min. To the reaction solution was added with 4-(4-fluorobenzyl)morpholin-2-ylmethylamine (1.2 mmol), and stirred for 30 min at a room temperature and then for an additional 4 hrs under reflux. The reaction mixture was cooled to a room temperature, and washed with saturated aqueous sodium hydrogen carbonate solution and then with saturated saline. After water was removed with a desiccant, the resulting solution was concentrated in a reduced pressure. In order to obtain a desired fraction, the residue was subjected to silica column chromatography (mobile phase: 30 (v/v) % Hexane in EA) to afford the title compound (Total yield: 53.0%)1H NMR (CDCl3) δ 8.20 (d, 1H), 8.12 (d, 1H), 7.54 (d, 1H), 7.36-7.24 (m, 7H), 7.01 (t, 2H), 6.46-6.38 (m, 1H), 4.08-3.98 (m, 1H), 3.87 (d, 1H), 3.73-3.61 (m, 4H), 3.53 (s, 2H), 3.45 (s, 2H), 3.32-3.19 (m, 2H), 2.85-2.61 (m, 4H), 2.32-2.14 (m, 3H), 2.08-1.88 (m, 3H) ppm.

Workup

  1. temperaturefor an additional 4 hrs under reflux
  2. temperatureThe reaction mixture was cooled to a room temperature
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. customAfter water was removed with a desiccant, the resulting solution
  5. concentrationwas concentrated in a reduced pressure
  6. customIn order to obtain a desired fraction

Sources & evidence

ORD record
ord-513bb944bcea4781b66f081a0e710a33
Source dataset
uspto-grants-2016_01
Patent number
US09227955B2

Reaction notes

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