3-[1-(1-indanylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole → 3-[1-(1-Indanylmethyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole

HRID 275703Notes

Reaction equation

HRID 275703 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([C:16]([N:18]2[CH2:23][CH:22]=[C:21]([C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][CH:25]=3)[CH2:20][CH2:19]2)=O)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1>C1COCC1>[CH:7]1([CH2:16][N:18]2[CH2:19][CH:20]=[C:21]([C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][CH:25]=3)[CH2:22][CH2:23]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 185458823-[1-(1-indanylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 185459843-[1-(1-Indanylmethyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of LiAlH4 (1.6 g) in dry THF (100 ml) kept at 0° C. was added drop-wise a solution of 3-[1-(1-indanylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole 4a (4.7 g) in dry THF (200 ml). The mixture was left stirring over-night at room temperature. Excess LiAlH4 was destroyed by cautiously adding 10% water in THF. The precipitated inorganic salts were filtered off. The solvents were evaporated leaving crude title compound (5.2 g). Recrystallization from 2-propanol afforded 2.8 g of pure 5a. Mp 168-170° C. 1H NMR (CDCl3): δ1.85-2.00 (m, 1H); 2.30-2.45 (m, 1H); 2.60 (dd, 1H); 2.60-2.70 (m, 2H); 2.70-3.00 (m, 5H); 3.30 (broad t, 2H); 3.45 (quin, 1H); 6.25 (broad t, 1H); 7.10-7.25 (m, 6H); 7.30-7.40 (m, 2H); 7.90 (d, 1H); 8.10 (broad s, 1H). MS m/z (%): 329 (MH+, 2%), 160 (10%), 131 (100%), 91 (19%).

Workup

  1. customkept at 0° C.
  2. waitThe mixture was left
  3. customExcess LiAlH4 was destroyed
  4. additionby cautiously adding 10% water in THF
  5. filtrationThe precipitated inorganic salts were filtered off
  6. customThe solvents were evaporated
  7. customleaving crude title compound (5.2 g)
  8. customRecrystallization from 2-propanol

Sources & evidence

ORD record
ord-e758e3b83801441d8927cb3430f111a8
Source dataset
uspto-grants-2002_03
Patent number
US06352988B2

Reaction notes

Loading…