Morpholine → 4-(Cyclohex-2-en-1-yl)morpholine

HRID 1934876

反応式

HRID 1934876 の反応式
[CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>C1(C)C=CC=CC=1.C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].FC(F)(F)C(O)=O>[CH:2]1([N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH2:1][CH2:6][CH2:5][CH:4]=[CH:3]1

参加物

7

反応物 2

HCID 8083MorpholineHCID 116051,3-Cyclohexadiene

生成物 1

HCID 2587754-(Cyclohex-2-en-1-yl)morpholine収率 82%

試薬・触媒・溶媒 4

HCID 6422Trifluoroacetic acid触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6433264Bis(1,5-cyclooctadiene)nickel触媒HCID 1140Toluene溶媒

実験手順

Ni(cod)2 (11.0 mg, 0.040 mmol) and DPPF (44.0 mg, 0.080 mmol) were suspended in 0.3 mL of toluene in a screw-capped vial. The vial was sealed with a cap containing a PTFE septum and removed from the dry box. 1,3-Cyclohexadiene (160 mg, 2.00 mmol), morpholine (183 mg, 2.10 mmol) and trifluoroacetic acid (9.0 mg, 0.080 mmol) were added to the reaction mixture by syringe. The reaction mixture was stirred at room temperature for 14 h. The volatile compounds were evaporated under reduced pressure, and the residue was adsorbed onto silica gel. The product was eluted with 90% ethyl acetate/hexenes to give 274 mg (82%) of 4-(2-cyclohexenyl)morpholine: 1H NMR (500 MHz, [D]chloroform, 25° C.): δ=5.84-5.83 (m, 1H; H-C3), 5.68-5.66 (m, 1H; H-C2), 3.74-3.72 (m, 4H; CH2), 3.17 (brs, 1H; H-C1), 2.64-2.56 (m, 4H; CH2), 2.00-1.98 (m, 2H; CH2), 1.82-1.80 (m, 2H; CH2), 1.57-1.54 (m, 2H; CH2); 13C{1H} NMR (125 MHz, [D]chloroform, 25° C.): δ=130.08, 128.77, 67.34, 60.22, 49.12, 25.15, 23.07, 21.29.

後処理

  1. customThe vial was sealed with a cap
  2. customremoved from the dry box
  3. customThe volatile compounds were evaporated under reduced pressure
  4. washThe product was eluted with 90% ethyl acetate/hexenes

出典と根拠

ORDレコード
ord-a9a0f616734643878c5906c6c192735b
出典データセット
uspto-grants-2002_05
特許番号
US06384282B2

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