Dimethylamine → HCID 13787827, 화합물

HRID 2106890노트

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HRID 2106890 반응식
C=O.CNC.[S:6](=[O:10])(=[O:9])([OH:8])[OH:7].S(O)(O)(=O)=O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:24]2([CH2:31][CH2:32][CH3:33])[CH:29]=[CH:28][N:27]([CH3:30])[CH2:26][CH2:25]2)[CH:21]=[CH:22][CH:23]=1.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([C:42]2([CH2:49][CH2:50][CH3:51])[CH:47]=[CH:46][N:45]([CH3:48])[CH2:44][CH2:43]2)[CH:39]=[CH:40][CH:41]=1.[OH-].[Na+]>O.CCCCCC>[S:6]([OH:10])([OH:9])(=[O:8])=[O:7].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:24]2([CH2:31][CH2:32][CH3:33])[CH:25]=[CH:26][N:27]([CH3:30])[CH2:28][CH2:29]2)[CH:21]=[CH:22][CH:23]=1.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([C:42]2([CH2:49][CH2:50][CH3:51])[CH2:43][CH2:44][N:45]([CH3:48])[CH:46]=[C:47]2[CH2:26][N:27]([CH3:30])[CH3:28])[CH:39]=[CH:40][CH:41]=1

참가 물질

10

반응물 6

HCID 674Dimethylamine2회HCID 712FormaldehydeHCID 1118Sulfuric Acid3회HCID 14798Sodium HydroxideHCID 13671256HCID 13671256, 화합물HCID 70357437HCID 70357437, 화합물

생성물 2

HCID 13787827HCID 13787827, 화합물HCID 70357437HCID 70357437, 화합물

시약·촉매·용매 2

HCID 962Water용매2회HCID 8058Hexane용매

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온도
30 °C

실험 절차

To a solution of 10 g (0.123 mol) of 37% aqueous formaldehyde and 15 g (0.133 mol) of 40% aqueous dimethylamine in 100 ml of water was added enough concentrated sulfuric acid so as to adjust the pH of the reaction mixture to 3-4. A solution of 25 g (0.0867 mol) of 1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1-methyl-4-propylpyridine sulfate in approximately 40 ml of water was added and the pH adjusted to 3-3.5, if necessary, by the addition of sulfuric acid or 40% aqueous dimethylamine. The 1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1-methyl-4-propylpyridine sulfate solution was prepared by the extraction of 25 g of 1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1-methyl-4-propylpyridine in 50 ml of hexane with a total of about 40 ml of 2.5N sulfuric acid. The mixture was stirred at approximately 65°-70° C. for 2 hours while maintaining the pH of the reaction mixture between 3-3.5. The solution was cooled to 30° C. and added to 100 ml of 25% sodium hydroxide. The resulting suspension was extracted twice with 50 ml portions of hexane. The organic extracts were combined and washed five times with 50 ml portions of water, one time with a 50 ml portion of saturated sodium chloride and dried over 5 g of anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure afforded 28.4 g of crude 1,4,5,6-tetrahydro-4-(3-methoxyphenyl)-N,N,I-trimethyl-4-propyl-3-pyridinemethanamine as an oil. Purity 85% by NMR. Yield 92.3%. m/e Theory calculated for C19HY30N2O: 302.2376; Found 302.2394. NMR: (CDCl3) δ0.92 (3H,t), 2.17 (6H,s), 2.63 (3H,s), 3.78 (3H,s), 6.10 (1H,s), 6.7-7.2 (4H,m,aryl). 13C NMR: (CDCl3) δ14.92(q), 18.11(t), 36.32(t), 40.16(t), 43.03(q), 43.47(s), 45.80(q), 46.28(t), 55.11(q), 60.80(t), 109.02(s), 110.32(d), 114.33(d), 120.68(d), 128.52(d), 136.64(d), 151.65(s), 159.24(s).

후처리

  1. temperaturewhile maintaining the pH of the reaction mixture between 3-3.5
  2. extractionThe resulting suspension was extracted twice with 50 ml portions of hexane
  3. washwashed five times with 50 ml portions of water, one time with a 50 ml portion of saturated sodium chloride
  4. dry with materialdried over 5 g of anhydrous sodium sulfate
  5. customEvaporation of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-3458f275c4fd47cf892e1446b5c7ee33
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04931558

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