Formaldehyde → HCID 59242117, compound

HRID 1876211Notes

Reaction equation

HRID 1876211 reaction equation
Cl.[CH2:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH3:12])=[CH:7][C:6]=1[F:13])[CH3:3].C(O[C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=1F)C.[NH:25]1[C:29]2C=CC=C[C:28]=2[N:27]=N1.[CH2:34]=O.[BH4-].[Na+]>>[NH2:27][CH2:28][C:29]1[N:25]=[C:12]([N:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:2][CH3:3])=[C:6]([F:13])[CH:7]=2)[CH3:34])[C:19]2[C:20](=[CH:21][CH:22]=[CH:17][CH:18]=2)[N:23]=1

Participants

6

Reactant 5

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 195992054-Ethoxy-3-fluoroanilineHCID 68516737HCID 68516737, compoundHCID 178418385HCID 178418385, compound

Product 1

HCID 59242117HCID 59242117, compound

Procedure

(4-Ethoxy-3-fluoro-phenyl)-methyl-amine hydrochloride: The free base of the title compound was synthesized as a clear, pale tan liquid by a procedure similar to that found in Example 221 from 4-ethoxy-3-fluoro-phenylamine (1.828 g, 11.78 mmol), 1H-benzotriazole (1.407 g, 11.8 mmol), 37 wt % aq formaldehyde (0.90 mL, 12.1 mmol) and sodium borohydride (447 mg, 11.8 mmol); with purification by MPLC (SiO2/0-33% EtOAc in hexanes). The title compound was obtained as an off-white solid after concentrating a soln of the free base in HCl-i-PrOH in vacuo. LC-MS (ESI+; 170 ([M+H]+)).

Workup

  1. customwith purification by MPLC (SiO2/0-33% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4e021e2338e44b24a957d777fb065319
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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