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Phenol → HCID 10222398, 화합물

HRID 1582454
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HRID 1582454 반응식
[CH2:1]([N:8]1[CH2:24][CH2:23][C:12]2=[C:13]([CH2:20][CH2:21][OH:22])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[N:11]2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]1(O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:1]([N:8]1[CH2:24][CH2:23][C:12]2=[C:13]([CH2:20][CH2:21][O:22][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[N:11]2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

6

반응물 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10268002HCID 10268002, 화합물

생성물 1

HCID 10222398HCID 10222398, 화합물수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(Chart D, Step 3): A dry round bottom flask is charged with 2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanol (420 mg, 1.31 mmol), phenol (185.2 mg, 1.97 mmol), triphenylphosphine (413 mg, 1.57 mmol), and THF (12 mL, freshly distilled). After cooling the reaction to 0° C., diethylazodicarboxylate (DEAD) (0.248 mL, 1.57 mmol) is added dropwise via syringe. The ice bath is allowed to expire, and the reaction is stirred at ambient temperature for 18 hours. The reaction is quenched with 30% H2O2 (0.20 mL), diluted with ethyl ether and washed twice with 10% aq. NaHSO3. The organics are washed twice with aq. 1N NaOH, once with brine, dried with Na2SO4, filtered and concentrated to 1.08 g of a crude yellow solid. Purification of the crude using silica gel and 10% ethyl acetate in heptane as the eluent gives 392 mg (76%) of 3-benzyl-11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a pale yellow oil. HRMS (FAB) calculated for C27H28N2O+H1 397.2280, found 397.2271.

후처리

  1. distillationfreshly distilled)
  2. temperatureAfter cooling
  3. customthe reaction to 0° C.
  4. customThe reaction is quenched with 30% H2O2 (0.20 mL)
  5. additiondiluted with ethyl ether
  6. washwashed twice with 10% aq. NaHSO3
  7. washThe organics are washed twice with aq. 1N NaOH, once with brine
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to 1.08 g of a crude yellow solid
  11. customPurification of the crude

출처 및 근거

ORD 기록
ord-f06eae3902ad49d4be85bf7b34e56914
출처 데이터셋
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06734301B2

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