Benzylamine → N-(7-methyl-1,4-dioxaspiro[4.5]dec-8-ylidene)-1-phenylmethanamine

HRID 1970976노트

반응식

HRID 1970976 반응식
CCN(CC)CC.[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:16][CH:17]1[C:26](=O)[CH2:25][CH2:24][C:19]2([O:23][CH2:22][CH2:21][O:20]2)[CH2:18]1.CC(OC)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:16][CH:17]1[C:26](=[N:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:25][CH2:24][C:19]2([O:20][CH2:21][CH2:22][O:23]2)[CH2:18]1

참가 물질

7

반응물 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 2706287-Methyl-1,4-dioxaspiro[4.5]decan-8-one

생성물 1

HCID 67536022N-(7-methyl-1,4-dioxaspiro[4.5]dec-8-ylidene)-1-phenylmethanamine

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of NEt3 (560 mL, 4.02 mol) and benzylamine (131 mL, 1.20 mol) in CH2Cl2 (500 mL) was added TiCl4 (500 mL of 1.0 M solution in CH2Cl2, 0.500 mol) over 30 min while the internal temperature was kept below −10° C. The resulting dark red suspension was stirred at −20° C. to −30° C. for 15 min, then a solution of 7-methyl-1,4-dioxaspiro[4.5]decan-8-one (170 g, 1.00 mmol) in CH2Cl2 (500 mL) was added at −10° C. The resulting grey-yellow suspension was allowed to warm to room temperature over 2 h, then stirred at room temperature for 16 h. MTBE (1.0 L) was added to the reaction mixture, and the yellow suspension was stirred at room temperature for 30 min and filtered through a pad of Solka Floc. The cake was washed with MTBE (4×500 mL), and the combined filtrates were concentrated to provide N-(7-methyl-1,4-dioxaspiro[4.5]dec-8-ylidene)-1-phenylmethanamine, which was used directly in the next step.

후처리

  1. customwas kept below −10° C
  2. stirringstirred at room temperature for 16 h
  3. stirringthe yellow suspension was stirred at room temperature for 30 min
  4. filtrationfiltered through a pad of Solka Floc
  5. washThe cake was washed with MTBE (4×500 mL)
  6. concentrationthe combined filtrates were concentrated

출처 및 근거

ORD 기록
ord-9c4e65b9df92429fa27ef8e2dcb0b653
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431569B2

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