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Acetic Acid → Ammonia methanol dichloromethane

HRID 33700
ノート
印刷プレビュー

反応式

HRID 33700 の反応式
Cl.[N:2]1([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:50][CH:51]([Cl:53])C>>[NH3:2].[CH3:10][OH:11].[Cl:50][CH2:51][Cl:53].[CH2:24]([N:21]1[CH2:20][CH2:19][N:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][CH2:8][N:2]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]3)=[CH:13][CH:14]=2)[CH2:23][CH2:22]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 99240121-[4-(3-Piperidin-1-yl-propoxy)-phenyl]-piperazine hydrochloride

生成物 2

HCID 101111911-Benzyl-4-[4-(3-piperidin-1-yl-propoxy)-phenyl]-piperazine
HCID 21584172
Ammonia methanol dichloromethane
収率 5%

実験手順

A solution of the product of Example 25 (151 mg), benzaldehyde (54 mg), and acetic acid (24 mg) in dichloroethane (3 mL) was treated with sodium triacetoxyborohydride (119 mg). After 14 h, the reaction was quenched with saturated aqueous sodium bicarbonate, and the aqueous phase was extracted with dichloromethane (120 mL). The organic phase was dried (magnesium sulfate) and evaporated in vacuo. Silica gel chromatography of the residue (5% 2M ammonia-methanol/dichloromethane) gave the title compound as an ivory solid (73 mg). 1H NMR (400 MHz, CDCl3): 7.36-7.24 (m, 5H), 6.89-6.80 (m, 4H), 3.94 (t, J=6.4 Hz, 2H), 3.56 (s, 2H), 3.08 (t, J=4.9 Hz, 4H), 2.61 (t, J=5.0 Hz, 4H), 2.48-2.44 (m, 2H), 2.39 (bs, 4H), 1.98-1.91 (m, 2H), 1.61-1.56 (m, 4H), 1.46-1.40 (m, 2H).

後処理

  1. customthe reaction was quenched with saturated aqueous sodium bicarbonate
  2. extractionthe aqueous phase was extracted with dichloromethane (120 mL)
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. customevaporated in vacuo

出典と根拠

ORDレコード
ord-0e86a1e79ddf41149078c1f9136e9e56
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07429586B2

反応ノート

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