Hydrochloric Acid → alpha-[1-(4-Chlorophenyl)cyclobutyl]benzylamine hydrochloride

HRID 35702

반응식

HRID 35702 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[Cl:9]C1C=CC(C2(C#N)CCC2)=CC=1.Cl[C:23]1[CH:24]=[C:25]([C:30]2([C:34]#[N:35])[CH2:33][CH2:32][CH2:31]2)[CH:26]=[CH:27][C:28]=1[Cl:29].[BH4-].[Na+].Cl>CCOCC.CO.O.C1(C)C=CC=CC=1>[ClH:9].[Cl:29][C:28]1[CH:27]=[CH:26][C:25]([C:30]2([CH:34]([NH2:35])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:33][CH2:32][CH2:31]2)=[CH:24][CH:23]=1

참가 물질

11

반응물 6

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrileHCID 4311764Sodium borohydrideHCID 5462224MagnesiumHCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrile

생성물 1

HCID 13083226alpha-[1-(4-Chlorophenyl)cyclobutyl]benzylamine hydrochloride

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 1140Toluene용매HCID 3283Diethyl Ether용매4회

실험 절차

A solution of bromobenzene (15.7 g) in ether (50 ml) was added dropwise with cooling to magnesium turning (2.4 g) under an atmosphere of nitrogen. A solution of 1-(4-chlorophenyl)-cyclobutanecarbonitrile (19.1 g) prepared in a similar manner to that described in Example 1 for the 1-(3,4-dichlorophenyl)cyclobutane carbonitrile in ether (50 ml) was added and the ether replaced by dry toluene (130 ml). The reaction mixture was heated on a steam bath for one hour. A sample (20 ml) of the resulting solution was added to a solution of sodium borohydride (1 g) in diethyleneglycoldimethyl ether (60 ml) and the mixture was stirred for one and a half hours. Water (60 ml) was added slowly and the aqueous layer extracted with toluene. The toluene extracts were washed with water, dried and evaporated to give a residue which was dissolved in methanol (50 ml). 6N Hydrochloric acid (5 ml) was added and the soltution filtered and evaporated. Trituration with dry acetone gave α-[1 -(4-chlorophenyl)cyclobutyl]benzylamine hydrochloride (m.p. 277°-279° C.) (Formula I R1 =Ph; R2 =H; R3, R4 =H; R5 =4--Cl; R6 =H).

후처리

  1. additionwas added
  2. temperatureThe reaction mixture was heated on a steam bath for one hour
  3. extractionthe aqueous layer extracted with toluene
  4. washThe toluene extracts were washed with water
  5. customdried
  6. customevaporated
  7. customto give a residue which
  8. filtrationthe soltution filtered
  9. customevaporated

출처 및 근거

ORD 기록
ord-76e9d160f9a34421912976577c642cd9
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04767790

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