Cyclopropanemethanamine → N-Cyclopropylmethyl-10,11-dihydro-5H-dibenzo-(a,d)-cyclohepten-5-imine

HRID 1076068

反応式

HRID 1076068 の反応式
[CH3:1][N:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2.[CH:18]1(CN)[CH2:20][CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH:18]1([CH2:1][N:2]=[C:3]2[C:4]3[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=3[CH2:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=3)[CH2:20][CH2:19]1

参加物

4

反応物 3

HCID 75646CyclopropanemethanamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 21541752N-methyl-10,11-dihydro5H-dibenzo[a,d]cyclohepten-5-imine

生成物 1

HCID 194091N-Cyclopropylmethyl-10,11-dihydro-5H-dibenzo-(a,d)-cyclohepten-5-imine収率 65%

実験手順

In a Carius tube is placed 4.52 g of N-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-imine, 9.2 g of cyclopropylmethylamine and 0.46 g of p-toluenesulfonic acid hydrate. The tube is sealed under vacuum and heated to 120° for 60 hours. The cooled tube is opened, the excess cyclopropylmethylamine is removed under vacuum, and the resiude is dissolved in ether. The solution is washed with aqueous sodium hydroxide solution and dried. The solvent is removed, and the residue is combined with the recovered cyclopropylmethylamine and 0.43 g of p-toluenesulfonic acid hydrate. The mixture is transferred to a Carius tube which is then sealed under vacuum and heated to 120° for an additional 30 hours to complete the reaction. The mixture is worked up as described above, and the crude product is crystallized from hexane to give 3.47 g (65%) of N-cyclopropylmethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-imine, mp 98°-99°. An analytical sample (hexane) had mp 99°-100°. Nmr spectrum (in CDCl3): multiplets at τ 2.1-3.0 (8H), 6.1-7.5 (6H), 8.3-9.0 (1H) and 9.1-10.0 (4H). Anal. Calcd. for C19H19N: C, 87.31; H, 7.33; N, 5.36; Found: C, 87.52; H, 7.27; N, 5.53.

後処理

  1. customThe tube is sealed under vacuum
  2. temperatureheated to 120° for 60 hours
  3. customthe excess cyclopropylmethylamine is removed under vacuum
  4. dissolutionthe resiude is dissolved in ether
  5. washThe solution is washed with aqueous sodium hydroxide solution
  6. customdried
  7. customThe solvent is removed
  8. customis then sealed under vacuum
  9. temperatureheated to 120° for an additional 30 hours
  10. customthe reaction
  11. customis crystallized from hexane

出典と根拠

ORDレコード
ord-57e751ab7f514bfd886450e800f033d3
出典データセット
uspto-grants-1976_05
特許番号
US03954865

関連ノート

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