Diethyl Ether → (+/-)-3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl)amino]propanenitrile

HRID 55369노트

반응식

HRID 55369 반응식
[OH-].C[N+:3](C)(C)[CH2:4][C:5]1C=CC=C[CH:6]=1.[C:13]1([CH2:19][NH:20][CH2:21][CH:22]2[CH2:27][CH2:26][C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[O:23]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O(CC)CC>C(#N)C=C>[O:23]1[C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[CH2:26][CH2:27][CH:22]1[CH2:21][N:20]([CH2:19][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:6][CH2:5][C:4]#[N:3]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 66854Benzyltrimethylammonium hydroxideHCID 10753388Benzyl-chroman-2-ylmethyl-amine; oxalic acid

생성물 1

HCID 18694181(+/-)-3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl)amino]propanenitrile수율 28.6%

시약·촉매·용매 1

HCID 7855Acrylonitrile용매

실험 절차

3 ml of N,N,N-trimethylbenzenemethanaminium hydroxide was added dropwise to a stirred mixture of 60 g (±)-3,4-dihydro-N-(phenylmethyl)-2H-1-benzopyran-2-methanamine in 350 ml of 2-propenenitrile. After stirring for 4 days at reflux temperature, the reaction mixture was cooled and poured into 1,1'-oxybisethane. The whole was filtered over diatomaceous earth and the filtrate was evaporated, yielding 21 g (28.6%) of (±)-3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl)amino]propanenitrile as crude residue (interm. 21).

후처리

  1. temperatureat reflux temperature
  2. temperaturethe reaction mixture was cooled
  3. filtrationThe whole was filtered over diatomaceous earth
  4. customthe filtrate was evaporated

출처 및 근거

ORD 기록
ord-1ab6bc44443b4496b30871ab02bad067
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624952

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