Dimethylamine → HCID 59600651, compound

HRID 2267106Notes

Reaction equation

HRID 2267106 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([C:23]([OH:25])=O)=[CH:15][CH2:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][NH:27][CH3:28].Cl.CN(C)CCCN=C=NCC.O.OC1C2N=NNC=2C=CC=1>CN(C=O)C.O>[CH3:26][N:27]([CH3:28])[C:23]([C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2([CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9][CH2:10]2)[CH2:14][CH:15]=1)=[O:25]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68681207HCID 68681207, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 59600651HCID 59600651, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the above crude carboxylic acid (300 mg, ca. 0.87 mmol), dimethylamine (2.0M in THF, 0.88 ml, 1.76 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 338 mg, 1.76 mmol), hydroxybenzotriazole hydrate (178 mg, 1.31 mmol) in DMF (10 ml) was stirred at room temperature for 24 h, poured into water, extracted with EtOAc (three times). The extracts were dried (Na2SO4), concentrated and purified by flash chromatography (hexane/EtOAc 1:0 to 0:1) to give tert-butyl 4-(dimethylcarbamoyl)-2H-spiro[naphthalene-1,4′-piperidine]-1′-carboxylate (B2) (156 mg). LC-MS: m/e=371.1 (M+H), 315.0 (M+H−C(CH3)3). Rt=3.16 min. 1H-NMR (500 MHz, CDCl3): 7.32-7.27 (m, 2H), 7.13 (t, 1H), 6.97 (d, 1H), 6.00 (t, 1 H), 3.91 (br. d, 2H), 3.04 (br. s, 3H), 2.97 (t, 2H), 2.85 (br. s, 3H), 2.44 (br. s, 2H), 1.85 (m, 2H), 1.70 (d, 2H), 1.40 (s, 9H).

Workup

  1. extractionextracted with EtOAc (three times)
  2. dry with materialThe extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by flash chromatography (hexane/EtOAc 1:0 to 0:1)

Sources & evidence

ORD record
ord-6d1098035d6e488aa4724acc902731cc
Source dataset
uspto-grants-2010_12
Patent number
US07858790B2

Reaction notes

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