Hydrochloric Acid → HCID 69017117, compound

HRID 1455076Notes

Reaction equation

HRID 1455076 reaction equation
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]4[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=O)=[CH:20][N:19]=4)[CH:13]=3)[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.C1COCC1.[ClH:33]>C1COCC1>[ClH:33].[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]4[N:19]=[CH:20][C:21]([CH2:22][NH2:24])=[CH:25][CH:26]=4)[CH:13]=3)[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]4[N:19]=[CH:20][C:21]([CH2:22][NH2:24])=[CH:25][CH:26]=4)[CH:13]=3)[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 69017758HCID 69017758, compound

Product 2

HCID 69017117HCID 69017117, compoundHCID 69017118HCID 69017118, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 6-(2-Phenylchroman-6-yloxy) nicotinamide (100 mg) in dry THF (2.0 ml) was added dropwise a solution of borane-THF complex (0.6 ml, 1.0 M in THF). The resulting mixture was refluxed for 4 hours. After cooling to the room temperature 3 M HCl solution was added and THE was evaporated in vacuum. The mixture was made alkaline with 50% NaOH-solution and extracted with ethyl acetate and dried. The hydrochloride of C-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]methylamine was obtained via treatment with HCL-ether solution. 1H NMR (400 MHz, d6-DMSO) δ: 8.29 (bs, 3H), 8.21 (s, 1H), 7.95 (d, 1H, J 8.5 Hz), 7.47-7.34 (m, 5H), 7.03 (d, 1H, J 8.5 Hz), 6.89-6.86 (m, 3H), 5.13 (d, 1H, J 8.4 Hz), 4.00 (m, 2H), 2.94 (m, 1H), 2.70 (m, 1H), 2.19 (m, 1H), 2.00 (m, 1H).

Workup

  1. temperatureThe resulting mixture was refluxed for 4 hours
  2. additionwas added
  3. customTHE was evaporated in vacuum
  4. extractionextracted with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-47db54c39c9d4744a8f1bbf7ae8fb25c
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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