Triethylamine → HCID 59730973, compound

HRID 416134Notes

Reaction equation

HRID 416134 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]2.[Br:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21](O)=[O:22])[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.O>[Br:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([NH:1][C:2]2[C:11]3[CH2:10][CH:9]([OH:12])[CH2:8][CH2:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)=[O:22])[CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 74653(3-Bromophenyl)acetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 230669958-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

Product 1

HCID 59730973HCID 59730973, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 8-amino-1,2,3,4-tetrahydro-naphthalen-2-ol (500 mg, 3.06 mmol) and 3-bromophenylacetic acid (725 mg, 3.37 mmol) in DMF was added triethylamine (465 mg, 4.60 mmol), l-hydroxybenzotriazole (497 mg, 3.68 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (705 mg, 3.68 mmol). The mixture was stirred for 16 hours at room temperature. To the product mixture was added water and extracted with ethylacetate. The organic layer was washed with aqueous HCl solution then aqueous NaOH solution and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The product was purified by silica gel column chromatography (hexane:acetone, 2:1) to afford 2-(3-bromophenyl)-N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)acetamide (130 mg, 12% yield).

Workup

  1. extractionextracted with ethylacetate
  2. washThe organic layer was washed with aqueous HCl solution
  3. dry with materialaqueous NaOH solution and brine, dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by silica gel column chromatography (hexane:acetone, 2:1)

Sources & evidence

ORD record
ord-8c873310dd134390af4253f6f75a3586
Source dataset
uspto-grants-2012_01
Patent number
US08088826B2

Reaction notes

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