Tert-Butylamine → HCID 19027240, compound

HRID 2258277Notes

Reaction equation

HRID 2258277 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[CH:17]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([NH2:27])([CH3:26])([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[CH:17]=[N:27][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 98176132-(8-Phenyloctyl)benzaldehyde

Product 1

HCID 19027240HCID 19027240, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 2-(8-phenyloctyl)benzaldehyde (10 g, 0.034 mol), and t-butylamine (4.96 g, 0.068 mol) in toluene (100 mL) was refluxed under standard Dean-Stark conditions for 16 h. The solution was evaporated to an oil which was vacuum distilled (bp 260° C., 0.15 mm Hg) to afford the titled product (11.1 g, 94%): GC RT 19.8 min (DB-1, 30 m×0.53 mm, program, 100° C. for 5 min, 100°-260° C. at 15° C./min, hold at 260° C. for 12 min.); 1H NMR (CDCl3, 400 MHz) δ 8.58 (s, 1H), 7.86 (d, J=7.5 Hz, 1H), 7.29-7.13 (m, 8H), 2.79 (t, J=7.5 Hz, 2H), 2.58 (t, J=7.5 Hz, 2H), 1.59-1.51 (m, 12H), 1.30 (s, 9H).

Workup

  1. customThe solution was evaporated to an oil which
  2. distillationdistilled (bp 260° C., 0.15 mm Hg)

Sources & evidence

ORD record
ord-387fb93bcead4d4db2714a598e506e40
Source dataset
uspto-grants-1997_08
Patent number
US05659084

Reaction notes

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