Ammonia → N,N-Dimethyl-3,4-dioleyloxybenzylamine

HRID 638772ノート

反応式

HRID 638772 の反応式
Cl.[CH3:2][NH:3][CH3:4].[CH2:5]([O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:27]=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[BH4-].[Na+].N>C(O)C.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[CH3:2][N:3]([CH2:27][C:26]1[CH:29]=[CH:30][C:31]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[C:24]([O:23][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:25]=1)[CH3:4]

参加物

7

反応物 4

HCID 222AmmoniaHCID 10473Dimethylamine, hydrochlorideHCID 4311764Sodium borohydrideHCID 161030163,4-Dioleyloxybenzaldehyde

生成物 1

HCID 23642188N,N-Dimethyl-3,4-dioleyloxybenzylamine

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 702Ethanol溶媒

実験手順

To a solution of triethylamineamine (2.0 mL, 14 mmol) in ethanol (20 mL) was added dimethylamine hydrochloride (1.63 g, 20 mmol), titanium tetraisopropoxide (5.96 mL, 20 mmol) and 3,4-dioleyloxybenzaldehyde (6.39 g, 10 mmol). The mixture was allowed to stir under argon for 10 h at room temperature. Sodium borohydride (0.57 g, 15 mmol) was added to the reaction mixture which was then allowed to stir at room temperature overnight. Concentrated aqueous ammonia (4 mL) was added slowly to the reaction mixture. The reaction mixture was filtered and the solids washed with dichloromethane. The filtrate was dried over K2CO3, filtered and concentrated. The resultant oil was purified via flash chromatography (2-10% acetone in dichloromethane, 0.5% TEA gradient) to afford 5.81 g (87-+%) of a yellow oil.

後処理

  1. stirringto stir at room temperature overnight
  2. filtrationThe reaction mixture was filtered
  3. washthe solids washed with dichloromethane
  4. dry with materialThe filtrate was dried over K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant oil was purified via flash chromatography (2-10% acetone in dichloromethane, 0.5% TEA gradient)
  8. customto afford 5.81 g (87-+%) of a yellow oil

出典と根拠

ORDレコード
ord-3ed07e4e92d04d8fa9dd75535ac37a43
出典データセット
uspto-grants-2010_04
特許番号
US07691405B2

反応ノート

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