N-Benzyl-6-(3-phenylpropoxy)hexan-1-amine--hydrogen bromide (1/1) → HCID 19862676, compound

HRID 1165274Notes

Reaction equation

HRID 1165274 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]([NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])[CH:10]=1)=[O:4].Br.[C:26]1([CH2:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][NH:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[OH:4][CH:3]([C:5]1[CH:6]=[CH:7][C:8]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]([NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])[CH:10]=1)[CH2:2][N:42]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33][CH2:32][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 19798064N-Benzyl-6-(3-phenylpropoxy)hexan-1-amine--hydrogen bromide (1/1)HCID 19862709HCID 19862709, compound

Product 1

HCID 19862676HCID 19862676, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl N-[5-bromoacetyl-2-(phenylmethoxy)phenyl]carbamate (0.58 g), N-[6-(3-phenylpropoxy)hexyl]benzenemethanamine hydrobromide (0.66 g) and DEA (0.48 g) in dichloromethane (15 ml) was stirred at room temperature under nitrogen for 26 h. Dichloromethane (50 ml) was added, the solution washed successively with 2N hydrochloric acid (50 ml), water (50 ml), 8% sodium bicarbonate solution (50 ml), dried and evaporated in vacuo. The residual brown oil (1.02 g) in absolute ethanol (20 ml) at 0° was treated with sodium borohydride (0.15 g), and the mixture was allowed to warm up to room temperature and stirred under nitrogen for 18 h. 2N Hydrochloric acid (5 ml) was cautiously added, the mixture stirred at room temperature for 5 min and evaporated in vacuo. The residue was partitioned between 8% sodium bicarbonate solution (10 ml) and EA (20 ml) and the organic phase dried and evaporated in vacuo to give a yellow oil. Purification by FCC on triethylamine deactivated silica (40 g) eluting with ER-CX (7:3) gave the title compound as a colourless oil (0.84 g).

Workup

  1. washthe solution washed successively with 2N hydrochloric acid (50 ml), water (50 ml), 8% sodium bicarbonate solution (50 ml)
  2. customdried
  3. customevaporated in vacuo
  4. additionThe residual brown oil (1.02 g) in absolute ethanol (20 ml) at 0° was treated with sodium borohydride (0.15 g)
  5. addition2N Hydrochloric acid (5 ml) was cautiously added
  6. stirringthe mixture stirred at room temperature for 5 min
  7. customevaporated in vacuo
  8. customThe residue was partitioned between 8% sodium bicarbonate solution (10 ml) and EA (20 ml)
  9. customthe organic phase dried
  10. customevaporated in vacuo
  11. customto give a yellow oil
  12. customPurification by FCC on triethylamine deactivated silica (40 g)
  13. washeluting with ER-CX (7:3)

Sources & evidence

ORD record
ord-6f471a350e4146fe998da076c01dbc44
Source dataset
uspto-grants-1990_03
Patent number
US04908386

Reaction notes

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