Triethylamine → HCID 72309465, compound

HRID 2400553Notes

Reaction equation

HRID 2400553 reaction equation
[CH3:1][O:2][C:3]1([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[CH2:6][O:5][CH2:4]1.Cl.[NH2:16][OH:17].C(N(CC)CC)C>C(O)C>[OH:17][N:16]=[C:11]([C:10]1[CH:9]=[CH:8][C:7]([C:3]2([O:2][CH3:1])[CH2:6][O:5][CH2:4]2)=[CH:14][CH:13]=1)[NH2:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59504617HCID 59504617, compound

Product 1

HCID 72309465HCID 72309465, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(3-methoxyoxetan-3-yl)benzonitrile (Step 1, 500 mg, 2.64 mmol), hydroxylamine hydrochloride (403 mg, 5.81 mmol) and triethylamine (810 μL, 5.81 mmol) in ethanol (12.5 mL) was stirred and heated at reflux for 2 h. After being cooled to rt, the reaction mixture was evaporated to dryness. The resulting material was treated with a mixture of water (5 mL) and diethyl ether (0.5 mL). The solid was isolated by filtration, washed with a small amount of cold water and dried in a vacuum oven to afford the title compound as a colorless solid (520 mg, 86%): 1H NMR (400 MHz, DMSO-d6) δ 9.67 (s, 1H), 7.73 (d, 2H), 7.43 (d, 2H), 5.84 (broad s, 2H), 4.79-4.75 (m, 4H), 3.01 (s, 3H); DCI(NH3)-MS m/z 223 (MH)+; HPLC RT (Method I) 2.54 min.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. customthe reaction mixture was evaporated to dryness
  4. additionThe resulting material was treated with a mixture of water (5 mL) and diethyl ether (0.5 mL)
  5. customThe solid was isolated by filtration
  6. washwashed with a small amount of cold water
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-b3c8d02e067e409ab66a4578dcc0fa92
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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