Formaldehyde → HCID 86704394, compound

HRID 1427418Notes

Reaction equation

HRID 1427418 reaction equation
[CH2:1]=O.Cl.[CH2:4]([NH:11][CH2:12][CH2:13][CH2:14][Cl:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[P:16]([O-])([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17]>O1CCOCC1>[CH2:4]([N:11]([CH2:1][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:13][CH2:14][Cl:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5166299Diethyl phosphoric acidHCID 20570562N-Benzyl-3-chloropropan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 86704394HCID 86704394, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.6 mL of 37% aqueous formaldehyde solution is added to a suspension of N-benzyl-3-chloropropan-1-amine hydrochloride (7.9 g or 35.9 mmol) in dioxane (60 mL), the resulting mixture is slightly heated until it becomes a solution. The solution is cooled to room temperature, 3.2 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 7.6 g target compound (yield: 63%). The analytical data of the obtained product are as follows: 1HNMR (400 MHz, DMSO-d6): δ=7.30-7.21 (m, 5H), 4.01-3.93 (m, 4H), 3.69 (s, 2H), 3.59 (t, J=6.8 Hz, 2H), 2.83 (d, J=10.0 Hz, 2H), 2.61 (t, J=6.8 Hz, 2H), 1.85-1.82 (m, 2H), 1.2 (t, J=7.2 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-dadddb24e7624a369ac20a3c2c33ff24
Source dataset
uspto-grants-2015_01
Patent number
US08933230B2

Reaction notes

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