Morpholine → 3-Chloro-1-morpholin-4-yl-5,6,8a,9-tetrahydro-8H-7,10-dioxa-2,4,4b-triaza-phenanthrene

HRID 334140Notes

Reaction equation

HRID 334140 reaction equation
Cl[C:2]1[C:15]2[O:14][CH2:13][CH:12]3[N:7]([CH2:8][CH2:9][O:10][CH2:11]3)[C:6]=2[N:5]=[C:4]([Cl:16])[N:3]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C(N(CC)CC)C>>[Cl:16][C:4]1[N:3]=[C:2]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:15]2[O:14][CH2:13][CH:12]3[N:7]([C:6]=2[N:5]=1)[CH2:8][CH2:9][O:10][CH2:11]3

Participants

4

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 866673581,3-Dichloro-5,6,8a,9-tetrahydro-8H-7,10-dioxa-2,4,4b-triaza-phenanthrene

Product 1

HCID 866673593-Chloro-1-morpholin-4-yl-5,6,8a,9-tetrahydro-8H-7,10-dioxa-2,4,4b-triaza-phenanthreneYield 38%

Conditions

Temperature
140 °C

Procedure

A mixture of 1,3-dichloro-5,6,8a,9-tetrahydro-8H-7,10-dioxa-2,4,4b-triaza-phenanthrene (100 mg, 0.38 mmol), morpholine (80 μL, 0.92 mmol) and triethylamine (70 μL, 0.50 mmol) in IMS (5 mL) was heated at 140° C. for 25 mins in a microwave reactor, then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, 0 to 10 to 15 to 25% ethyl acetate in pentane) affording 3-Chloro-1-morpholin-4-yl-5,6,8a,9-tetrahydro-8H-7,10-dioxa-2,4,4b-triaza-phenanthrene (45 mg, 38%). LCMS (method A): RT=2.92 min, [M+H]+=313. 1H NMR (400 MHz, CDCl3): δ 4.37 (1H, dd, J=13.2, 3.0 Hz), 4.19 (1H, dd, J=10.8, 3.3 Hz), 3.99 (1H, dd, J=11.1, 3.9 Hz), 3.88 (1H, dd, J=10.8, 3.2 Hz), 3.80 (dd, J=11.1, 8.4 Hz), 3.75 (4H, m), 3.66-3.53 (6H, m), 3.24 (1H, t, J=11.1 Hz), 3.00 (1H, m).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was purified by column chromatography (SiO2, 0 to 10 to 15 to 25% ethyl acetate in pentane)

Sources & evidence

ORD record
ord-de3a30dc63a944aaa69cef40eab023e4
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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