Morpholine → HCID 12083036, compound

HRID 1168510Notes

Reaction equation

HRID 1168510 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([CH:11]=O)[CH:2]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[N:13]1([CH2:11][C:3]2[CH:2]=[N:1][C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[CH:4]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 120830355,6,7,8-tetrahydroquinoline-3-carbaldehyde

Product 1

HCID 12083036HCID 12083036, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A 100 mL three-neck round bottom flask equipped with a nitrogen inlet, bubbler, and glass stopper is charged with 1,2-dichloroethane (45 mL), 5,6,7,8-tetrahydroquinoline-3-carbaldehyde (Preparation 15, 2.39 g) and morpholine (1.42 mL). To the above solution is added NaBH(OAc)3 (5.01 g) in one portion. After 1 hour at room temperature, the reaction is quenched via slow addition of Na2CO3 (50 mL of a saturated aqueous solution). The resulting biphasic solution is stirred for two hours at room temperature then poured into methylene chloride (100 mL). The resulting layers are separated, and the organic layer is dried with Na2SO4, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography (10% methanol/CH2Cl2) to give 2.60 g (76%) of the title compound as an oil which crystallizes on standing. Physical characteristics: M.p. 40.9° C.; 1H NMR (CDCl3): δ8.24, 7.31, 3.68, 3.41, 2.88, 2.74, 2.41, 1.87, 1.78; 13C NMR (CDCl3) δ156.4, 147.5, 137.6, 131.9, 130.1, 66.9, 60.4, 53.5, 32.2, 28.7, 23.1, 22.7.

Workup

  1. customA 100 mL three-neck round bottom flask equipped with a nitrogen inlet
  2. customthe reaction is quenched via slow addition of Na2CO3 (50 mL of a saturated aqueous solution)
  3. additionthen poured into methylene chloride (100 mL)
  4. customThe resulting layers are separated
  5. dry with materialthe organic layer is dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by flash chromatography (10% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-32b8f66440054d2498109d4af1bf7760
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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