1-Adamantanecarboxylic acid → Tricyclo(3.3.1.13,7)decane-1-carboxamide

HRID 1700043

반응식

HRID 1700043 반응식
[C:1]12([C:11]([OH:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([N:16](C(F)(F)C(F)C(F)(F)F)CC)C>N>[C:1]12([C:11]([NH2:16])=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

참가 물질

5

반응물 3

HCID 132351-Adamantanecarboxylic acidHCID 136149N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamineHCID 178435160HCID 178435160, 화합물

생성물 1

HCID 21686Tricyclo(3.3.1.13,7)decane-1-carboxamide

시약·촉매·용매 1

HCID 222Ammonia용매

실험 절차

1-Adamantanecarboxylic acid (10.8 g, 0.06 mole) was added to N,N-diethyl-1,1,2,3,3,3-hexafluoropropylamine (13.4 g, 0.06 mole) contained in a wide mouth polyethylene bottle with magnetic stirring. The acid dissolved immediately during which time a highly exothermic reaction occurred. The reaction mixture was allowed to cool to room temperature and cold aqueous ammonia (250 ml) was added slowly. A heavy precipitate of the amide appeared almost immediately. After the addition was complete, the reaction mixture was stirred for about fifteen minutes. The 1-adamantanecarboxamide was collected and washed copiously with water followed by ethyl ether and dried. Yield: 10.7 g, 100%; mp 189.4-190.2° C. (Lit. mp 189° C., Stetter, et. al., Chem. Ber., 1960, 226-230). The analytical sample was recrystallized from cyclohexane and sublimed. Anal. Calcd. for C11H17NO: C, 73.76; H, 9.49; N, 7.82. Found: C, 73.67; H. 9.60; N, 7.78.

후처리

  1. dissolutionThe acid dissolved immediately during which time
  2. customa highly exothermic reaction
  3. additionAfter the addition
  4. customThe 1-adamantanecarboxamide was collected
  5. washwashed copiously with water
  6. customdried
  7. customThe analytical sample was recrystallized from cyclohexane

출처 및 근거

ORD 기록
ord-f332560369fb4a529b72203584c66332
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06348625B1

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