Phosphorus oxychloride → HCID 178478198, compound

HRID 1492191Notes

Reaction equation

HRID 1492191 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][C:2]1=O.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.P(Cl)(Cl)([Cl:23])=O>C(#N)C>[ClH:23].[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[N:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 669533-MorpholinoneHCID 7357562-Morpholinoaniline

Product 1

HCID 178478198HCID 178478198, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of 3-morpholinone (4 g) in dry acetonitrile (40 ml), 4-(2-aminophenyl)morpholine (3.6 g) in dry acetonitrile (20 ml) and phosphorous oxychloride (3.6 ml) was heated for 40 hours at 65°-70° C. to give oil which was purified by column chromatography on neutral alumina (72 g) using (a) hexane, (b) dichloromethane:hexane (1:1) and (c) dichloromethane as eluant. The resulting oil was treated with a saturated solution of hydrogen chloride in methanol (25 ml) to give a pale yellow solid which was recrystallised from a 1:1 mixture of methanol and ether to give 4-[2-(3-morpholinylideneamino)phenyl]-morpholine hydrochloride (m.p. 262°-263° C.).

Workup

  1. customto give oil which
  2. customwas purified by column chromatography on neutral alumina (72 g)
  3. additionThe resulting oil was treated with a saturated solution of hydrogen chloride in methanol (25 ml)
  4. customto give a pale yellow solid which
  5. customwas recrystallised from a 1:1 mixture of methanol and ether

Sources & evidence

ORD record
ord-32be69fe9dcf42aab300f5aea813480b
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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