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Hydrochloric Acid → HCID 18663626, 화합물

HRID 1956560
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HRID 1956560 반응식
Br[CH2:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1.[CH2:18]([NH2:21])[CH:19]=[CH2:20].COC(C)(C)C.[ClH:28]>CO.C(OCC)C.C(OCC)(=O)C>[ClH:28].[CH2:18]([NH:21][CH2:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1)[CH:19]=[CH2:20].[CH2:18]([NH:21][CH2:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1)[CH:19]=[CH2:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 7853AllylamineHCID 15413tert-Butyl methyl etherHCID 18663590HCID 18663590, 화합물

생성물 2

HCID 1006131010-Allylaminomethyldibenz[b,f]oxepineHCID 18663626HCID 18663626, 화합물수율 39%

시약·촉매·용매 3

HCID 887
Methanol
용매
HCID 3283Diethyl Ether용매
HCID 8857Ethyl Acetate용매

실험 절차

At 50° C. a solution of 0.5 ml (1.74 mmol) of 10-bromomethyl-dibenz[b,F]oxepine is squirted into a solution of 0.3 ml (4 mmol) of allylamine in 0.9 ml of anhydrous methanol and the mixture is stirred for 30 minutes. Tert-butyl methyl ether and ethyl acetate are added and the mixture is extracted 3× with 20 ml of 1N hydrochloric acid each time, the combined aqueous phases are rendered basic with potassium hydroxide pellets and extracted 2× with ethyl acetate, and the organic phases are dried over sodium sulfate and concentrated. 0.35 ml (0.7 mmol) of 2N ethereal hydrochloric acid is added to the crude amine (180 mg) in 2 ml of diethyl ether, and the precipitated white hydrochloride is washed with diethyl ether and dried under a high vacuum at 40° C. 200 mg (667 μmol)=39% of the title compound alias 10-allylaminomethyl-dibenz[b,f]oxepine are obtained in the form of white crystals; melting point: 148°-158° C.; 1H-NMr (CD3OD, 200 MHz). 3.74 (d, 2H); 4.35 (d, 2H), 5.55 (m, 2H); 5.95 (m, 1H); 7.20-7.58 (m, 9H); MS: 263 (M+, free base), 222, 208, 181, 165, 152.

후처리

  1. customAt 50° C.
  2. extractionthe mixture is extracted 3× with 20 ml of 1N hydrochloric acid each time
  3. extractionextracted 2× with ethyl acetate
  4. dry with materialthe organic phases are dried over sodium sulfate
  5. concentrationconcentrated
  6. washthe precipitated white hydrochloride is washed with diethyl ether
  7. customdried under a high vacuum at 40° C

출처 및 근거

ORD 기록
ord-936fc637f31144c18c097e4bdb7c27b5
출처 데이터셋
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05780500

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