Acetic Acid → 6-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]-N-propyl-3-pyridinamine

HRID 327418

반응식

HRID 327418 반응식
[CH:1](=O)[CH2:2][CH3:3].[C:5]1([C:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19]#[C:20][C:21]3[N:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=3)[CH2:15][CH:16]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:5]1([C:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]#[C:20][C:21]3[N:26]=[CH:25][C:24]([NH:27][CH2:1][CH2:2][CH3:3])=[CH:23][CH:22]=3)[CH2:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 100863486-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]-3-pyridinamine

생성물 1

HCID 199601496-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]-N-propyl-3-pyridinamine

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

A solution of propionaldehyde (0.18 mL, 2.5 mmol), 6-[4-(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]-3-pyridinamine (Example 13) (0.83 g, 2.7 mmoL) and glacial acetic acid (0.14 mL, 2.5 mmol) in 20 mL of dichloroethane is treated with sodium triacetoxyborohydride (0.79 g, 3.7 mmol) under nitrogen and is stirred at room temperature for 18 hours. The reaction is quenched with saturated aqueous sodium bicarbonate, diluted with dichloromethane, and the organic layer is dried (sodium sulfate) and concentrated under reduced pressure. The residue is chromatographed (silica gel, 1% methanol/99% dichloromethane) to give the title compound, containing 0.20 mol of water; mp 138°-139° C.

후처리

  1. customThe reaction is quenched with saturated aqueous sodium bicarbonate
  2. additiondiluted with dichloromethane
  3. dry with materialthe organic layer is dried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed (silica gel, 1% methanol/99% dichloromethane)

출처 및 근거

ORD 기록
ord-991b6fd6abbe4575995966e5a11eeeec
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05273977

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