Methylamine → HCID 11832555, compound

HRID 1070516Notes

Reaction equation

HRID 1070516 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5][N:6]1[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1.[CH3:17][NH2:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl.C(O)(=O)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH:18][CH3:17])[CH2:8][CH2:7]1

Participants

8

Reactant 4

HCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 108487763,4-dichlorobenzyl-4-piperidone

Product 1

HCID 11832555HCID 11832555, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3,4-Dichloro-benzyl)-piperidin-4-one (3.1 g) in dichloromethane (50 ml) and acetic acid (0.69 ml) was added methylamine (6 ml of a 1M solution in tetrahydrofuran). The mixture was stirred for 5 minutes before the addition of sodium triacetoxyborohydride (3 g) and the resulting mixture stirred for 72 hours. Sodium bicarbonate solution (100 ml) added and the mixture stirred vigorously for 5 minutes before extraction of the product with dichloromethane (2×200 ml). The organics were separated, bulked and dried, (MgSO4). Purification by Biotage® 40S eluting 10%MeOH/0.5% 800 ammonia/dichloromethane gave the sub-title compound (1.8 g).

Workup

  1. customThe organics were separated
  2. customdried
  3. customPurification by Biotage® 40S
  4. washeluting 10%MeOH/0.5% 800 ammonia/dichloromethane

Sources & evidence

ORD record
ord-778e4a7017d04db6915eaf088f5f4f55
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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