Water → 3-(8-Ethyl-naphthalen-1-yl)-propane-1,2-diamine

HRID 1159183Notes

Reaction equation

HRID 1159183 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][CH:8]([CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH2:22][CH3:23])[CH:15]=[CH:14][CH:13]=1)[C:9]#[N:10].O.[OH-].[Na+]>C1COCC1>[CH2:22]([C:20]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:21]=1[C:12]([CH2:11][CH:8]([NH2:7])[CH2:9][NH2:10])=[CH:13][CH:14]=[CH:15]2)[CH3:23]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57543207HCID 57543207, compound

Product 1

HCID 575431993-(8-Ethyl-naphthalen-1-yl)-propane-1,2-diamineYield 28.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of LiAlH4 (117 mg) in THF (2 ml) was cooled to 0° C. and treated under an argon atmosphere with a solution of (RS)-2-amino-3-(8-ethyl-naphthalen-1-yl)-propionitrile (230 mg) in THF (4 ml). The reaction mixture was stirred for 5 hrs at r.t., then treated sequentially at 0° C. with 0.1 ml H2O, 0.1 ml 4N NaOH and 0.5 ml H2O. After stirring for 30 min, the solid was filtered off and washed with THF. The filtrate was concentrated. The crude product was isolated by column chromatography (silica gel; eluent: CH2Cl2→CH2Cl2/MeOH 9:1) to give 3-(8-ethyl-naphthalen-1-yl)-propane-1,2-diamine (66 mg) as light brown oil. MS (ISP): 229.3 ((M+H)+).

Workup

  1. stirringAfter stirring for 30 min
  2. filtrationthe solid was filtered off
  3. washwashed with THF
  4. concentrationThe filtrate was concentrated
  5. customThe crude product was isolated by column chromatography (silica gel; eluent: CH2Cl2→CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-a09cb40fce2e47bc9bbdc71fc9fed21a
Source dataset
uspto-grants-2010_10
Patent number
US07812047B2

Reaction notes

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