Aniline → Ammonia dichloromethane

HRID 33711ノート

反応式

HRID 33711 の反応式
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:42]([Cl:44])[Cl:43]>C(O)(=O)C>[NH3:1].[CH2:42]([Cl:44])[Cl:43].[C:20]1([NH:19][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:12][CH:13]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

8

反応物 5

HCID 6115AnilineHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

生成物 2

HCID 9945134Phenyl-[4-(3-piperidin-1-yl-propoxy)-benzyl]-amineHCID 22731429Ammonia dichloromethane収率 1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of the product of Example 9 (277 mg), aniline (108 mg), and acetic acid (0.07 mL) in DCM (5 mL) was treated with sodium triacetoxyborohydride (340 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (10 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (256 mg). 1H NMR (400 MHz, CDCl3): 7.27 (m, 2H), 7.18 (m, 2H), 6.88 (m, 2H), 6.72 (m, 2H), 6.64 (m, 2H), 4.24 (s, 2H), 4.00 (t, J=6.6 Hz, 2H), 3.94 (br, 1H), 2.48 (m, 2H), 2.41 (br, 4H), 1.98 (m, 2H), 1.64-1.57 (m, 4H), 1.48-1.41 (m, 2H).

後処理

  1. extractionextracted with DCM (3×10 mL)
  2. dry with materialThe combined organic phases were dried (sodium sulfate)
  3. customevaporated

出典と根拠

ORDレコード
ord-866d04a957dd4fc19548c453ec1cc881
出典データセット
uspto-grants-2008_09
特許番号
US07429586B2

反応ノート

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