Formaldehyde → HCID 18426185, compound

HRID 133625Notes

Reaction equation

HRID 133625 reaction equation
[C:1]([BH3-])#[N:2].[Na+].N[C:6]1[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][C:7]=1[C:8]([NH:10][CH2:11][C:12]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)=[O:13])=[O:9].[CH2:35]=O.[OH-].[Na+]>ClCCl.CO.C(#N)C.C(O)(=O)C>[Br:34][C:31]1[CH:32]=[CH:33][C:6]([N:2]([CH3:1])[CH3:35])=[C:7]([CH:30]=1)[C:8]([NH:10][CH2:11][C:12]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)=[O:13])=[O:9]

Participants

9

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 508820HCID 508820, compoundHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18426185HCID 18426185, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium cyanoborohydride (26 mg, 0.42 mmol) and acetic acid (14 mL) were added to a mixture of 4-[N-(2-amino-5-bromobenzoyl)glycyl]aminomethyl-1-(4-chlorobenzyl)piperidine (Compd. No. 1042) (67 mg, 0.14 mmol) with a 37% aqueous solution of formaldehyde (0.112 mL, 1.4 mmol), acetonitrile (2 mL) and methanol (1.5 mL), and the resulting mixture was stirred at 50° C. for 30 hours. A 1 M aqueous solution of NaOH and dichloromethane were added to the mixture. The aqueous layer was separated, and the organic layer was dried over K2CO3, filtered, concentrated and purified by column chromatography (SiO2, 20% methanol/ethyl acetate) to afford 4-[N-[5-bromo-2-(dimethylamino)benzoyl]glycyl]aminomethyl-1-(4-chlorobenzyl)piperidine (Compd. No. 1428) (60 mg, 82%). The purity was determined by RPLC/MS (100%). ESI/MS m/e 523 (M++H, C24H30BrClF6N4O2).

Workup

  1. customThe aqueous layer was separated
  2. dry with materialthe organic layer was dried over K2CO3
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography (SiO2, 20% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-0ae598602a474a5f86467b0d59043faa
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

Loading…