Formaldehyde → HCID 86704395, compound

HRID 1427419Notes

Reaction equation

HRID 1427419 reaction equation
[CH2:1]=O.[Cl:3][CH2:4][CH2:5][CH2:6][NH:7][CH3:8].[P:9]([O-])([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])=[O:10]>O1CCOCC1>[Cl:3][CH2:4][CH2:5][CH2:6][N:7]([CH2:1][P:9]([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])=[O:10])[CH3:8]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5418743-chloro-N-methylpropan-1-amineHCID 5166299Diethyl phosphoric acid

Product 1

HCID 86704395HCID 86704395, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.8 mL of 37% aqueous formaldehyde solution is added to suspension of 3-chloro-N-methylpropan-1-amine (1.4 g or 1.3 mmol) in dioxane (30 mL), the resulting mixture is slightly heated until it becomes a solution. The solution is cooled to room temperature, 1.6 mL of diethyl phosphate is added thereto, stirring at room temperature for 30 min, and then stirring at 90-100° C. for 3 h, the reaction is completed. The solvent is removed under reduced pressure, and the residue is purified by column chromatography (eluent: 1-4% MeOH in DCM) to obtain 2.3 g target compound (yield: 81%). The analytical data of the obtained product are as follows: 1HNMR (400 MHz, CDCl3): δ=4.17-4.10 (m, 4H), 3.74-3.53 (m, 4H), 3.28-3.08 (m, 2H), 2.80 (s, 3H), 2.25-2.09 (m, 2H), 1.29 (t, J=6.8 Hz, 6H).

Workup

  1. temperaturethe resulting mixture is slightly heated until it
  2. stirringstirring at 90-100° C. for 3 h
  3. customThe solvent is removed under reduced pressure
  4. customthe residue is purified by column chromatography (eluent: 1-4% MeOH in DCM)

Sources & evidence

ORD record
ord-816dfa2830ce41c781457563e177f4ed
Source dataset
uspto-grants-2015_01
Patent number
US08933230B2

Reaction notes

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