Triethylamine → hexahydro-1-[[4-(phenylmethoxy)phenyl]methyl]-1H-1,4-diazepine

HRID 16511

反応式

HRID 16511 の反応式
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:18]1([CH2:17][O:16][C:13]2[CH:12]=[CH:11][C:10]([CH2:9][N:1]3[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)=[CH:15][CH:14]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 68163Hexahydro-1,4-diazepineHCID 700424-Benzyloxybenzyl chlorideHCID 516892Sodium Bicarbonate

生成物 1

HCID 11197238hexahydro-1-[[4-(phenylmethoxy)phenyl]methyl]-1H-1,4-diazepine収率 78.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of hexahydro-1H-1,4-diazepine (3.44 g, 34.4 mmol) and 1-(chloromethyl)-4-(benzyloxy)benzene (2.0 g, 8.6 mmol) was treated with triethylamine (4.8 ml, 34.4 mmol) in 100 mL tetrahydrofuran and heated at reflux for 4 h. After cooling, the mixture was treated with saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Flash chromatography gave 2.0 g of hexahydro-1-[[4-(phenylmethoxy)phenyl]methyl]-1H-1,4-diazepine; 1H NMR (300 MHz, CDCl3) δ 7.44 (d, 2H), 7.39 (dd, 2H), 7.32 (dd, 1H), 7.26 (d, 2H), 6.93 (d, 2H), 5.05 (s, 2H), 3.60 (s, 2H), 2.96 (m, 2H), 2.89 (m, 2H), 2.68 (m, 2H), 2.65 (m, 2H), 1.75 (m, 2H) ppm.

後処理

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. temperatureAfter cooling
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7b63ce0800b14aa2be9ea3cff8245e13
出典データセット
uspto-grants-2010_06
特許番号
US07737145B2

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