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

HRID 53650

Reaction equation

HRID 53650 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

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 20) (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.

Workup

  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)

Sources & evidence

ORD record
ord-6401e278add04c6080f07f800a18b1a1
Source dataset
uspto-grants-1997_04
Patent number
US05620988

Linked notes

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