1,2-Dichloroethane → Ammonia dichloromethane

HRID 456948ノート

反応式

HRID 456948 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.[ClH:19].[CH3:20][NH:21][CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].ClC[CH2:41][Cl:42]>C(O)(=O)C>[NH3:1].[CH2:41]([Cl:42])[Cl:19].[CH3:20][N:21]([CH3:22])[CH2:15][C:14]1[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:12][CH:13]=1

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

生成物 2

HCID 9835304Dimethyl-[4-(3-piperidin-1-yl-propoxy)-benzyl]-amineHCID 22731429Ammonia dichloromethane収率 3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of the product of Example 9 (175 mg), dimethylamine hydrochloride (64 mg), and acetic acid (0.05 mL) in DCE (3 mL) was treated with sodium triacetoxyborohydride (210 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (1 mL) and extracted with DCM (3×3 mL). The combined organic phases were dried (magnesium sulfate) and evaporated. Chromatography of the residue (3% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (70 mg). 1H NMR (400 MHz, CDCl3): 7.19 (d, J=8.6 Hz, 2H), 6.85 (d, J=8.6 Hz, 2H), 3.99 (t, J=6.4 Hz, 2H), 3.35 (s, 2H), 2.50–2.35 (m, 6H), 2.22 (s, 6H), 2.01–1.94 (m, 2H), 1.63–1.55 (m, 4H), 1.46–1.40 (m, 2H).

後処理

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

出典と根拠

ORDレコード
ord-d72aa23dc6e241c0a8dccca700e25a1a
出典データセット
uspto-grants-2007_03
特許番号
US07186732B2

反応ノート

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