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

HRID 1934876

반응식

HRID 1934876 반응식
[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

참가 물질

7

반응물 2

HCID 8083MorpholineHCID 116051,3-Cyclohexadiene

생성물 1

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

시약·촉매·용매 4

HCID 6422Trifluoroacetic acid촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 6433264Bis(1,5-cyclooctadiene)nickel촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a9a0f616734643878c5906c6c192735b
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384282B2

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