Ethanolamine → HCID 68380401, compound

HRID 2364975Notes

Reaction equation

HRID 2364975 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[O:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17]O)=[CH:4][CH:3]=1.Cl[CH2:20][CH2:21][O:22][C:23]1[C:32]2C(=CC=C(F)C=2)[CH:26]=[CH:25][CH:24]=1.[NH2:34][CH2:35][CH2:36][OH:37].[C:38](=[O:41])(O)[O-].[Na+].C[N:44](C)C=O>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[O:12][CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][N:34]3[C:38](=[O:41])[C:22]([C:23]4[O:24][C:25]([CH3:26])=[N:44][CH:32]=4)=[CH:21][CH:20]=[C:35]3[C:36]2=[O:37])=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 700EthanolamineHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 68379766HCID 68379766, compoundHCID 68380172HCID 68380172, compound

Product 1

HCID 68380401HCID 68380401, compound

Conditions

Temperature
80 °C

Procedure

Synthesis of 2-({2-[(7-fluoronaphthalen-1-yl)oxy]ethyl}amino)ethanol (C41). A solution of 1-(2-chloroethoxy)-7-fluoronaphthalene (C40) (429 mg, 1.59 mmol) in N,N-dimethylformamide (8.9 mL) was treated with 2-aminoethanol (1.03 mL, 18.6 mmol) and heated to 80° C. for 18 hours. The reaction was cooled to room temperature, treated with saturated aqueous sodium bicarbonate solution (100 mL) and extracted with ethyl acetate (3×75 mL). The combined organic layers were washed with aqueous sodium hydroxide (1 M), dried over sodium sulfate and concentrated in vacuo. Purification via silica gel chromatography afforded the title compound as a colorless solid. Yield: 194 mg, 0.77 mmol, 48%. 1H NMR (400 MHz, CDCl3) δ 2.92-2.97 (m, 2H), 3.19 (dd, J=5.3, 5.1 Hz, 2H), 3.69-3.73 (m, 2H), 4.27 (dd, J=5.3, 5.1 Hz, 2H), 6.87 (d, J=7.6 Hz, 1H), 7.25-7.30 (m, 1H, assumed; partially obscured by solvent peak), 7.34 (dd, J=8.1, 7.7 Hz, 1H), 7.44 (d, J=8.2 Hz, 1H), 7.80 (dd, J=9.1, 5.6 Hz, 1H), 7.85 (dd, J=10.5, 2.5 Hz, 1H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate (3×75 mL)
  3. washThe combined organic layers were washed with aqueous sodium hydroxide (1 M)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-e1ea87d009fd489d8033a4107b85f0ed
Source dataset
uspto-grants-2014_04
Patent number
US08697673B2

Reaction notes

Loading…