Benzylamine → HCID 21104663, compound

HRID 1354218Notes

Reaction equation

HRID 1354218 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[N:31]=[CH:30][CH:29]=[C:28]2[CH2:35][CH2:36][CH:37]1[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]1.[O:44]=[C:45]1[NH:50][C:49]2[CH:51]=[C:52](C=O)[CH:53]=[CH:54][C:48]=2[O:47][CH2:46]1>ClC(Cl)C.C1COCC1>[CH2:1]([N:8]([CH2:9][C:53]1[CH:52]=[CH:51][C:49]2[NH:50][C:45](=[O:44])[CH2:46][O:47][C:48]=2[CH:54]=1)[CH:40]1[CH2:41][CH2:42][CH:37]([CH2:36][CH2:35][C:28]2[C:27]3[C:32](=[CH:33][CH:34]=[C:25]([O:24][CH3:23])[CH:26]=3)[N:31]=[CH:30][CH:29]=2)[CH2:38][CH2:39]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 107736383-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehydeHCID 21104620HCID 21104620, compound

Product 1

HCID 21104663HCID 21104663, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzylamine (0.135 ml, 1.24 mmol) and sodium triacetoxyborohydride (0.315 g, 1.55 mmol) were added to a solution of 4-[2-(6-methoxy-quinolin-4-yl)-ethyl]-cyclohexanone (Example 26.e) (0.35 g, 1.23 mmol) in dichloroethane (8 ml). The reaction mixture was stirred for 2 hours. 3-Oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde (0.230 g, 1.3 mmol), THF (4 ml and sodium triacetoxyborohydride (0.315 g, 1.55 mmol) was added. The reaction mixture was stirred overnight and then filtered over Hydromatrix (wetted with an NaHCO3 solution, 10 ml) and subsequently washed with dichloromethane. The filtrate was concentrated to dryness by rotary evaporation. The residue was purified by column chromatography on silica gel (dichloromethane/MeOH 19/1).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. filtrationfiltered over Hydromatrix (
  3. washsubsequently washed with dichloromethane
  4. concentrationThe filtrate was concentrated to dryness by rotary evaporation
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane/MeOH 19/1)

Sources & evidence

ORD record
ord-c13cebcbb571418aa2733909e64f19af
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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