Ammonium Chloride → HCID 54493135、化合物

HRID 2248120ノート

反応式

HRID 2248120 の反応式
[Cl:1][C:2]1[CH2:3][N:4]=[CH:5][C:6]2([CH3:19])[CH:17]([CH3:18])[CH:15]3[CH2:16][C:10]4=[C:11]([NH:14]3)[CH2:12][CH2:13][C:7]2=[C:8]4[CH:9]=1.C(N(C(C)C)CC)(C)C.[CH:29]1([CH2:32]Br)[CH2:31][CH2:30]1.[Cl-].[NH4+]>C(OCC)(=O)C.CN(C)C=O>[Cl:1][C:2]1[CH2:3][N:4]=[CH:5][C:6]2([CH3:19])[CH:17]([CH3:18])[CH:15]3[CH2:16][C:10]4=[C:11]([N:14]3[CH2:32][CH:29]3[CH2:31][CH2:30]3)[CH2:12][CH2:13][C:7]2=[C:8]4[CH:9]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 81503Bromomethylcyclopropane2 回HCID 81531DiisopropylethylamineHCID 73656239HCID 73656239、化合物

生成物 1

HCID 54493135HCID 54493135、化合物収率 32%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 2.2 g of 10-chloro-6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo[3,2-h][3]-benzazocine and 40 ml of dimethylformamide was added 3.2 ml of diisopropylethyl amine and 1.07 ml of cyclopropylmethyl bromide, under nitrogen. The reaction mixture was warmed in an oil bath maintained at 70°-77° C. Additional cyclopropylmethyl bromide (0.16 ml) was added, warming continued for a total of 3 hr, and the solution was poured into dilute aqueous ammonium chloride solution and ethyl acetate. The layers were separated and the aqueous layer extracted with ethyl acetate and ether. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate and filtered. The filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, 2% triethylamine/0-5% methanol/ethyl acetate) followed by recrystallization from ether/dichloromethane/pentane to afford 0.97 g (32%) of product. The product was combined with products from two other reactions. The combined material was recrystallized from dichloromethane and the sublimed (175°-180° C., about 0.2 mm) to give the analytical sample, mp 187°-190° C.

後処理

  1. temperatureThe reaction mixture was warmed in an oil bath
  2. temperaturemaintained at 70°-77° C
  3. temperaturewarming
  4. customcontinued for a total of 3 hr
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with ethyl acetate and ether
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous potassium carbonate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. customThe residue was purified by flash column chromatography (silica gel, 2% triethylamine/0-5% methanol/ethyl acetate)
  12. customfollowed by recrystallization from ether/dichloromethane/pentane

出典と根拠

ORDレコード
ord-235b7b227406440192f48066bccdd168
出典データセット
uspto-grants-1991_08
特許番号
US05037985

反応ノート

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