Water → n-Methyl-1-(1-methyl-1h-indol-5-yl)methanamine

HRID 1711828

반응식

HRID 1711828 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[CH3:13][NH2:14].[BH4-].[Na+].O>CO>[CH3:13][NH:14][CH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[CH:3]=[CH:4]2

참가 물질

6

반응물 4

HCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 75375341-methyl-1H-indole-5-carbaldehyde

생성물 1

HCID 18525753n-Methyl-1-(1-methyl-1h-indol-5-yl)methanamine수율 100%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

N-Methylindole-5-carbaldehyde (800 mg, 5.1 mmol) was dissolved in anhydrous methanol (15 mL). Methylamine (7.15 mL of 2M solution in methanol, 15.3 mmol) was added and the reaction was stirred for 3 hr. The solution was concentrated to a yellow oil and then dissolved into anhydrous methanol (15 mL). Sodium borohydride (194 mg, 5.1 mmol) was added and the mixture was stirred overnight. Water (1 mL) was added and the solution was concentrated to an orange oil. Sodium hydroxide (5 mL, 1N) was added and the product was extracted with ethyl acetate (3×20 mL), dried over MgSO4 and concentrated to afford the title compound as an orange oil (885 mg, 100%). 1H NMR (200 MHz, CDCl3) δ 7.57(s, 1H), 7.35-7.11(m, 3H), 6.51 (d, J=2.9 Hz, 1H), 3.85 (s, 2H), 3.79 (s, 3H), 2.48 (s, 3H).

후처리

  1. concentrationThe solution was concentrated to a yellow oil
  2. dissolutiondissolved into anhydrous methanol (15 mL)
  3. stirringthe mixture was stirred overnight
  4. concentrationthe solution was concentrated to an orange oil
  5. additionSodium hydroxide (5 mL, 1N) was added
  6. extractionthe product was extracted with ethyl acetate (3×20 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-21504158dc084497ad3ae3acd4fdeae6
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790709B2

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