Hydrochloric Acid → 6-(Hydroxymethyl)-N-(2-piperidinoethyl)-3-cyclohexene-1-carboxamide

HRID 566426

反応式

HRID 566426 の反応式
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[C@@H:10]12[C:19](=O)[O:18][C:16](=[O:17])[C@@H:11]1[CH2:12][CH:13]=[CH:14][CH2:15]2.[BH4-].[Na+].Cl>O.CC(O)C>[OH:18][CH2:19][CH:10]1[CH:11]([C:16]([NH:1][CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)=[O:17])[CH2:12][CH:13]=[CH:14][CH2:15]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 33944N-(2-Aminoethyl)piperidineHCID 98495Tetrahydrophthalic anhydride, cis-HCID 4311764Sodium borohydride

生成物 1

HCID 212661176-(Hydroxymethyl)-N-(2-piperidinoethyl)-3-cyclohexene-1-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3776Isopropanol溶媒

反応条件

温度
140 °C

実験手順

N-(2-Aminoethyl)piperidine (2.11 g) was added to cis-4-cyclohexene-1,2-dicarboxylic anhydride (2.50 g) and stirred for 6 hours at 140° C. The reaction mixture was suspended into a mixed solution of 2-propanol (125 ml) and water (21 ml) and then sodium borohydride (3.12 g) was added thereto at room temperature. After being stirred for 68 hours at room temperature, the reaction mixture was acidified with dilute hydrochloric acid and then concentrated. The residue was adjusted to pH 9 with saturated sodium hydrogencarbonate aqueous solution and 1N sodium hydroxide, and then extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate anhydride, and concentrated, thereby yielding a crude (3.34 g) containing the entitled compound as brown syrup.

後処理

  1. customat room temperature
  2. stirringAfter being stirred for 68 hours at room temperature
  3. concentrationconcentrated
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over sodium sulfate anhydride
  7. concentrationconcentrated
  8. customyielding a crude (3.34 g)

出典と根拠

ORDレコード
ord-c1fd2ea043c24870adbe68e0b74e7971
出典データセット
uspto-grants-2001_01
特許番号
US06174885B1

関連ノート

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